


If I Loved You Less

by surlybobbies



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Jane Austen Fusion, Demisexual Castiel (Supernatural), Emma by Jane Austen, Fluff, Humor, M/M, Minor Aaron Bass/Dean Winchester, Minor Charlie Bradbury/Gilda, Minor Daphne Allen/Castiel, Minor Eileen Leahy/Sam Winchester, Misunderstandings
Language: English
Status: Completed
Published: 2018-10-17
Updated: 2018-10-17
Packaged: 2019-08-03 11:24:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 26,948
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16325285
Author URL: https://archiveofourown.org/users/surlybobbies/pseuds/surlybobbies
Summary: (Inspired by Jane Austen’s Emma)Dean Winchester has everything.  He’s got a great house, a steady job, a beautiful car, a loyal best friend, and (most importantly) an abundance of great advice.  He wants nothing more than for everybody else in his life to know what it feels like to be as happy as he is.After successfully seeing his brother Sam married off to Eileen Leahy, Dean turns his attention to his newest friend: Charlie Bradbury.  Despite his best friend Cas’s apprehensions, Dean does his best to improve her life.  Thing is, none of his attempts at matchmaking seem to work.  In fact, Dean’s carefully laid plans for Charlie (and for himself) quickly start to fall apart.  Why is Charlie so oblivious?  And why is Dean so upset when Cas’s ex returns to town?Dean’s got a lot to learn about his family and friends, but mostly, he’s got a lot to learn about himself.(A modern-day Emma AU.)





	If I Loved You Less

**Author's Note:**

> It’s finally here! My first ever DCBB! I’m super excited for you to get into it, but first a few important notes:
> 
> 1) This is based off of Jane Austen’s novel Emma, which is by far my favorite of her novels and has produced some of my favorite Austen adaptations. Watch the BBC series if you want (starring Jonny Lee Miller) or the youtube series Emma Approved. They’re both fantastic. Of course, you should also read the original novel.
> 
> 2) In this fic, Dean is Emma and Cas is Knightley. They (along with all the other characters) have been made to fit the plot of Emma as best they could, but I didn’t want to sacrifice their characters just to fit into Austen’s plot, so there’ll be some (pretty obvious) digressions in personality, sexuality, and behavior.
> 
> 3) THE ART IS BY THE WONDERFUL BUSY SQUIRREL, who gave me three (3!!!!) pieces of art to go along with this fic, and I am so unbelievably happy I was paired with such a wonderful artist. You’ll see the art imbedded in the fic, and in the end notes, there’ll be a link to my DCBB masterpost (once it goes up) where you can find the rebloggable tumblr post for Busy’s art.

It occurred to Dean Winchester, as he watched his brother and new sister-in-law sway awkwardly on the dance floor of their wedding reception, that at that moment, he had everything he wanted. Sure, he wasn’t wealthy or famous, but Dean Winchester didn’t need money or fame to be content. No, all he needed was what he already had: a good job, his own place, a badass car, a wonderful mother, a loyal best friend, the biggest dork of a brother he could ask for, and now (finally) - a gorgeous, too-good-for-his-brother sister-in-law. 

The wedding and reception of Sam and Eileen Winchester took place outdoors. It was late spring, and the venue, an obscenely-priced private garden two hours from Dean’s home, had become a little too warm for Dean’s liking. He wanted to loosen his tie, but he knew that if his mother caught him, she would haul him back inside and fix it for him like he was 9 again, trying to skip out on some distant relative’s funeral service. 

Still, despite the temperature, the occasion was picture-perfect. An absurdly large fountain bubbled away somewhere behind Dean, and some of the guests were taking pictures in front of the tulip display a ways to his left. Also, Dean thought, smothering a self-congratulatory grin in his champagne flute, there was free alcohol. He was in such a good mood that for once he wasn’t even tempted to complain about the drink’s tiny serving.

Castiel Novak, Dean’s best friend, sighed to Dean’s right. When Cas sighed, it was always a full-body movement that heralded some sort of rebuke. Dean was in too good a mood to let that bother him either. 

He nudged Cas with an elbow and said, “Spit it out already.”

Cas leaned forward and stole Dean’s champagne flute from his hand. He drained it. He wiped at his mouth primly with a napkin then said, “Whatever you were thinking a few seconds ago was either inappropriate or ridiculous, and I suggest you stow it away for another occasion.”

Dean signaled a waiter for two refills of champagne. “How would you know what I was thinking?” he asked. The banter between him and Cas was playful, always playful, and the giddiness in Dean’s blood was pulling a grin to his mouth despite his best efforts.

“You were smiling into your champagne. You don’t like champagne.”

Dean finally turned toward Cas. Dean was the best man, but Cas had also been asked to stand by Sam’s side as a groomsman. He was dressed as Dean was: in a tailored grey suit with a pink hydrangea peeking out of a buttonhole. The tie was pink too, and it brought out the pink champagne flush on Cas’s cheeks. Dean was not so vain as to admit that Cas pulled off the colors much better than he did, so when he winked at Cas, it was a genuine compliment. “Why, gorgeous, I had no idea you paid so much attention.”

Cas rolled his eyes. “Save the sweet talk for someone it actually works on.”

The waiter came by with another round of champagne. Dean took a long draft of champagne. “See?” he said, placing the empty flute in front of him. “I love champagne.”

“If you say so,” Cas said, sipping politely at his own drink. His attention was now on Sam and Eileen, still swaying on the dance floor while other couples began to join them. Eileen was stifling laughter in Sam’s lapel. Cas was smiling at them, though he was trying to hide it, but Dean saw through the act anyhow. The infamous grump Castiel Novak showing his sentimental side - who knew?

“If you were curious, I was smiling because life’s good.” He slid his gaze to Cas to see if he was listening. “Life’s great, actually.”

“I wasn’t curious,” Cas said, though he had turned his attention back to Dean. “But since you’re in such a sharing mood, I’ll indulge you. Why is your life so great, Dean?”

Dean motioned to the dance floor in front of them. “See that? That’s my brother and his gorgeous new wife.”

Cas looked amused now. He nodded encouragingly. “Go on.”

“Well, I got them here, didn’t I?”

Cas sighed again, another sigh that seemed to emerge from the deepest part of his soul. Tiredly, he said, “For the last time, Dean Winchester, you did not get them together. Tripping Sam _accidentally_ did not get them married.”

“First,” Dean said, “it was _not_ an accident. Second, if you’re getting a drink, get me one too.”

Cas ignored the request and spoke very slowly, his finger poking at the white tablecloth with each word. “You tripped him - accidentally - and she grabbed his arm.”

“Then I _conveniently_ left them alone to get to know each other.”

“Because your food order was called. You didn’t do a thing.” He tugged down the hand that Dean was raising to get the attention of a waiter.

Dean shrugged him off. Nothing Cas said mattered. In fact, it mattered so little that Dean was going to prove him wrong. Somehow. 

He let the conversation lapse into silence as he cast his mind for a way to soothe his wounded pride. Eventually he called for another flute of champagne, and when the waiter brought it to him, Cas’s face pinched, but he didn’t say a word. Dean counted that as a win. 

Toward the end of the night, as Sam and Eileen were saying goodbye to the guests who came to wish them well one last time, and Dean’s alcohol-fueled heartburn was starting up, a guest caught his eye. She was a petite redhead, dwarfed by Sam, and she was patting away tears as she hugged Eileen next to the tulip display.

Cas had some time ago left Dean to his drinking and gone to speak to Eileen’s parents, and he had been conveniently replaced by Dean’s mom. He nudged her. “Who’s that?” he asked.

“The redhead?” Mary said, yawning. “I think it might be one of Eileen’s old classmates. Why do you ask?”

Dean watched as the redhead bid a final goodbye to Sam - he had to bend, and she was stretched to her tiptoes - and then walk away. She tripped on a stray chair leg, then looked around to see if anyone saw. Her eyes caught Dean’s. She smiled sheepishly, then turned away. ...Then she bumped into Cas and immediately started frantically apologizing.

Dean kissed his mom on the forehead. “Get home safe, alright? I’ll see you soon.”

The floor was swimming in front of him and he knew he’d have one hell of a headache tomorrow, but none of that mattered because at this moment, he had a mission - and hell if he wasn’t going to complete it.

 

The closer Dean got to the redhead the slower he felt he was moving. How much had he drank? Jesus. 

The parking lot was close to empty. He tried to call out, but whether or not he succeeded he had no idea because she wasn’t turning around. If anything she was walking faster. He sped up. Stumbled. Saw that she was reaching into her purse for her keys. He walked faster. He was within touching distance when the redhead suddenly whirled around and showed him the keys between her knuckles.

“Why are you following me?” she said shakily.

Dean wasn’t able to formulate a quick enough response to that, but a sticker on the car he assumed was hers gave him a smooth segue. “I like Hermione too.”

The redhead stared, shocked. “What does that have to do with anything?” She brandished her fist at him. “Leave me alone!”

A familiar voice called out from behind Dean. Cas. Good. He’d be able to see Dean’s success. Cas’s arm went around his middle. Inexplicably, Dean felt a little better.

“Charlie, he means no harm.”

“You know each other?” Dean asked at the same time Charlie did.

Cas heaved Dean up a little more securely against his side. “Charlie and I met a few minutes ago,” Cas said, then to Charlie, with a deep sigh that Dean felt all along his side, “Dean is regrettably my best friend. He is also regrettably drunk. I am so sorry.”

Dean mustered up what he hoped was his charming smile. “Sorry,” he repeated.

“Why were you following me?” Charlie asked, still sounding skeptical.

“I want to be your friend.” Even to his drunk ears, the proclamation made him cringe. “I mean. I - I like Hermione too. Emma Watson. Sexy.”

“For fuck’s sake,” Cas mumbled. “Charlie, we’ll wait for you to get in your car and then I’m taking this idiot home.”

But Charlie had finally lowered her fist. She was grinning a little cheekily. “Emma Watson is a babe, isn’t she?” 

 

Which is how Dean acquired the little sister he never knew he wanted. Charlie was Eileen’s old high school classmate. The women had never been close, but when they had run into each other at a mall a few weeks back, Eileen had been so touched by Charlie’s heartfelt congratulations that she’d extended an invitation to the wedding. 

Charlie was every bit as sweet as Eileen said she was. She was sweet and sincere and smart as a whip, and now that Sammy was all grown up and had Eileen to protect him, it felt right to fill that gap with the nerdy, cheerful Charlie. And just like he’d helped Sammy and Eileen, Dean was ready to help Charlie.

It’s not like Charlie hadn’t already done pretty well for herself. She had a steady job in IT, a pretty active social life, a _really_ active online life, several video game tournament trophies on her walls, and two cats named Xena and Gabrielle. She seemed content with her life. But Dean couldn’t help but think she seemed a little lost at times. A little lonely. 

“You’re just projecting,” Cas said, still tap-tapping away on his laptop. Cas was a semi-successful sci-fi novelist. He didn’t quite make enough to pay the bills, and he spent a considerable amount of effort budgeting, but he’d inherited just enough from his parents to survive. Still, Dean was not above dropping by with a bag full of takeout - just to make sure Cas was eating. The Mexican food from earlier was sitting uncomfortably in his stomach. 

“Yeah, sure,” Dean said, snorting derisively. “ _I’m_ the lonely one? _You’re_ the hermit.”

“You’re the one hanging out with the hermit,” Cas said blithely, not even looking up from his laptop screen. “In the hermit’s apartment.”

“It’s called philanthropy.”

Cas ignored him. Dean threw himself onto Cas’s couch - a hand-me-down and probably filthy - and stared up at the ceiling. 

“Anyhow,” he continued. “Good news.”

The typing stopped for a moment, just long enough for Cas to say, “You and I always seem to have different opinions about what constitutes ‘good news.’”

“I’ve figured out a way to help Charlie.”

The typing stopped for real this time. Dean angled his head so he could look at Cas behind him. He smiled at the slack-jawed incredulousness on Cas’s face. “Finally got you to pay attention to me.”

“Too many people pay attention to you, Dean,” Cas said, closing his laptop. “That’s how you became an arrogant asshole who thinks he can improve other people’s lives when they don’t need it.”

“Charlie needs it.”

Cas cleaned when he was stressed. It didn’t happen often, but when it did, it always seemed to be because of Dean, something Dean was quietly a little proud of. Cas wandered into his kitchen and grabbed a rag. “Charlie Bradbury is a perfectly well-adjusted young woman.”

“Doesn’t mean she doesn’t need a little help every now and then.”

Dean was secretly thrilled with the way Cas’s mouth pinched. He knew he shouldn’t like riling up Cas so much, but there was something about breaking Cas’s usually stoic expression that was addictive.

Cas didn’t reply to Dean’s comment. He had begun wiping down his kitchen counters, transferring dirty glasses into the sink and clearing what looked to be twelve days’ worth of notes from a stack near the fridge. His brows were furrowed, and the long lines of muscle under his tee contracted with every pass of the rag against the tile. 

“Did Charlie ask for your help?” 

Dean tore his eyes away from his best friend’s arms and looked back at the ceiling again. He didn’t want to sit up. He felt a confrontation coming and he wanted to stay cool. “People who need help don’t ask for help, dude. Take you, for example.”

There was a long pause. When Cas did speak, the room seemed deathly still. “And what, pray tell, do I need help with?” 

“You gotta relax, buddy. Find some way to let off steam. Get laid, maybe?”

At that, there was such a long pause that Dean almost thought Cas left the room, but when Dean finally lifted his head from the couch arm to see what happened, he saw Cas, sitting on a kitchen stool, staring at the floor with red cheeks and a furrowed brow. “I think it’s time you left, Dean.”

Dean’s stomach dropped. “What?” 

“I’m tired, and I’m tired of your so-called philanthropy. If you want to help Charlie with her nonexistent problems, go right ahead, but don’t be surprised if she throws you out too. Now please leave. Lock the door on your way out.” He walked into his bedroom, closed the door, and didn’t come back out.

 

Dean didn’t know where to begin apologizing to Cas. He didn’t even know what to apologize _for_. He had no idea what he’d done or said. Sure, he’d been a dick, and sure, he’d been doing it on purpose, but it was no more than he usually was around Cas, and Cas was generally just as much as a dick to him as well. 

He spent the rest of the afternoon dicking around his house, cleaning up, but it was only when he found himself wiping down his kitchen like Cas had been doing that he gave up. He dialed Sam. “I have a problem.”

“Why, thanks for the congratulations, Dean; it’s not like this is the first time I’ve heard from you since getting married.”

“Oh, fuck off, I was the first one to congratulate you.”

“I was under the impression you don’t remember much from that night.”

Dean scowled, but he couldn’t find a decent argument against that. He remembered flowers and Charlie and Cas and a hell of a lot of bubbles up his nose. “Whatever. Congratulations. Now will you help me figure out what I did to piss Cas off?”

“Wow,” Sam said, sounding vaguely impressed. “You do a lot of shit that _should_ piss him off, but I’ve never actually seen him pissed off. What did you do?”

“I wouldn’t be calling you if I knew, jackass.”

“Is that the way you should be speaking to the father of your niece or nephew?”

Dean stopped. He took a deep breath. “Is Eileen…?” It couldn’t be possible. It had only been a few weeks since the wedding; they’d have had no way of knowing. Unless - “Sam, you sly son of a bitch. What’ll Mom say?”

Sam gave a long-suffering sigh. “Stop. She’s not pregnant. At least I don’t think so. No, we’re - we’re getting a dog.”

At this, Dean laughed, and it was genuine. “No shit. Congratulations, bro.” Dean wasn’t a particular fan of animals, but he knew Sam had always dreamed of a white picket fence and 2.5 kids and a dog running around in the backyard. Dean’s little brother was halfway there. 

“Yeah,” Sam said, sounding wistful. “Gonna stop by the shelter tomorrow. Hopefully by the end of the week we’ll be able to take one home. You and Cas should stop by for dinner. Maybe we’ll have a little barbeque or something.”

Dean winced. “Fat chance of that happening, since Cas isn’t even talking to me.”

Sam sighed, and it reminded Dean so much of Cas that his heart started to ache a little bit. “Alright,” Sam said, “Tell me everything.”

Dean broke down their conversation, and Sam made sounds of irritation at the appropriate parts. Dean supposed he deserved it. 

When he was finished, Sam took a long, slow breath. “First,” he began, “You’re an asshole. Second, you really call yourself Cas’s best friend?”

Dean figured that was a rhetorical question, but to imply that he could be anything _but_ Cas’s best friend rubbed Dean the wrong way. “He’s being really fucking difficult, alright?”

Another sigh. “Dean, remember that night like - ten years ago? Cas told us he needed to talk to us and then he -”

“Yeah, I _know_ he’s asexual or whatever, dude, what’s the point?”

“Do you even know what ‘asexual or whatever’ means, Dean?”

“He’s not into sex. Big deal.”

“So you don’t know why he’d be upset when you tell him to go get laid so he’d relax more?”

Dean was beginning to get the picture, but it was still difficult to grasp. “It was a joke. People say it all the time.”

“I don’t think it would have mattered if someone else said it to him,” Sam said. “But _you_ said it to him. His _best friend_ implied that he had a problem and that to solve it he needed to get laid, like sex is the only solution to his problems. The world already glorifies sex, which is something he can’t relate to - ”

“He should know I don’t mean it like that - “

“He probably does know,” Sam said reasonably. “But he’s also trusted you for ten years with this big piece of him, and then you treat it like it’s no big deal.”

“But it isn’t a big deal,” Dean said. He felt his arguments crumbling. 

“Not to you. Because you care about him no matter what. But it’s a big deal to him, Dean, and you shouldn’t treat it like a joke.”

Dean wanted to scream into a pillow. He wanted to punch himself repeatedly in the face and _then_ scream into a pillow. He pinched the bridge of his nose. “Do you think that’s why he doesn’t date?”

“Because of the expectation of sex?” There was a long pause. “That’s probably one of the reasons.”

“One of the reasons?” Dean repeated. “Is there another secret that I should know about him?” Dean was being sarcastic, but when Sam hesitated, Dean felt at a loss. “Shit, Sammy. What am I missing?”

There was another, much longer, pause. “If there is another secret,” Sam said slowly, “He’ll tell you when he’s ready.”

“The hell? Sammy, I am up to here with all these goddamn secrets. What the hell do you know that I don’t?”

“Honestly? Nothing. Nothing for sure.”

“Jesus. Why do you people speak in riddles?”

“You’ll catch up eventually, Dean.”

 

Eileen texted later that week that she and Sam were having a small barbeque with their friends and family at their new place. She invited Dean and told him that Cas had already told her he would be there, then followed up that text with a kissy face and the words _Make up already._

 _Tried that,_ Dean messaged back, thinking of the call log on his phone that detailed exactly _how many_ times he’d tried to call Cas and gotten his voicemail. 

_Try again this weekend,_ She replied. _Bring alcohol. You can spend the night if you want._

_Got it. See ya, gorgeous._

_See ya, loser._

 

Sam and Eileen’s new place was just over an hour away from Dean’s. It was a little too far for Dean’s liking, but he figured Sammy deserved a little privacy after spending so much of his childhood sharing a bedroom with Dean.

He packed an overnight bag and a few six-packs into the trunk of the Impala and began the drive, wondering if Cas would be there by the time he arrived, and what he might say to him. It had been a little less than a week since they’d last spoken. While it wasn’t unusual to go so long without speaking, it was unusual to go so long without speaking _on purpose._ Sometimes Cas got caught up in his writing, and sometimes Dean got caught up with paperwork at the garage, but neither of them had ever knowingly just _stopped talking_ to the other one, and they’d been friends for fifteen years.

When Dean arrived, he saw Cas’s car already parked in front of Sam and Eileen’s home and steeled himself for an awkward night if none of Sam and Eileen’s other guests showed up for a while.

Dean stacked the six-packs in his arms and began the short walk to the porch. The house was a small one. There were only two bedrooms, both upstairs, but the property at least had a backyard, which had been high on Sam and Eileen’s list of priorities. It wasn’t their dream house, but it was perfect for the time being, and Dean had to admit that Sammy was doing a pretty good job with repairs. 

The porch was solid, too, which hadn’t been the case when Dean had first visited a few months back. He admired the plants that Eileen had set out, and smiled a little at the welcome mat: _Welcome to our home_ , it read. It was silly to get emotional over a welcome mat, especially one that they had probably purchased at the local Home Depot for ten bucks, but at that moment, Dean couldn’t help feeling overwhelmingly proud of his little brother. They had come a long way since living with their dad.

Feeling a little bad about it, Dean tapped the door twice with a shoe. “Hello? Can’t use my hands here!”

The door opened. Cas was on the other side of the threshold, staring at him. 

Dean heard Sam’s voice from the kitchen. “Hey, Dean, come in! Sorry, we’re trying to calm Willow down!”

Cas stepped away to let Dean through. 

“Thanks,” Dean mumbled. He started walking to the kitchen, but Cas’s voice stopped him.

“Do you - do you need help with that?”

Dean stopped and looked down at his arms. Three six-packs weren’t heavy. But he looked up at Cas and saw sincerity in the downturn of his best friend’s mouth. “Yeah, sure,” he said, and let Cas take one. “Thanks.”

Cas shrugged. He let Dean go ahead of him.

In the kitchen, Dean found Sam and Eileen crouched around the tiniest version of a pit bull that Dean had ever seen. It was sitting down and licking Sam’s hand, but then it saw Dean and jumped up to its four legs and started howling. It was the tiniest, cutest howl in the whole goddamn world, and Dean couldn’t help snorting in derision. “Do they put up stuffed animals for adoption now?”

Sam glared at him. “I know your shriveled little heart has never heard of puppies, Dean, so I’m going to let that one slide.” 

Dean, smirking, offloaded the six-packs into the fridge. Cas handed the last one to him. It felt like a win, like a sign of good things to come, so when he straightened and closed the fridge door, he held his hands out, nodding to the mess of ingredients on the counters. “C’mon,” he said, “Give her to me and Cas. You finish up here.”

“I - I didn’t agree to this,” Cas said. “I don’t know how to play with dogs.”

“Neither do I,” Dean said cheerfully. He took the dog from Eileen. It was laughably light. “Let’s go, Willow.”

 

They ended up in the backyard, sitting on the grass, throwing a too-big tennis ball for Willow the puppy and watching her stumble after it. The fences needed some new paint, Dean noted, but the yard was tended and Eileen had even started planting some flowers. Another wave of affection for his family hit him. He started laughing.

“What is it?” Cas said. It was the first thing either of them had said since sitting down.

Dean shrugged. “I’m just - Sammy’s done pretty well, hasn’t he? Gorgeous wife, decent neighborhood, a goddamn puppy. Damn. It’s his dream come true.”

Cas turned his head upward to the sun, closing his eyes against its glare. This time, when he sighed, it was happy. “I’m very happy for him,” he said.

“I’m over the moon for him.”

Cas smiled. He still kept his eyes closed. Not for the first time, Dean marveled at Cas’s profile. His best friend was an attractive man, and Dean suspected that even if he were straight, he’d still have trouble keeping his eyes off of Cas. He was magnetic.

A silence descended. Willow gave up on wrestling the ball back to Dean and eventually made her way to the shade under his legs. She was panting in the late spring warmth. Dean admired the roundness of her stomach, and when she caught him looking at her she stood up and barked. Her tail began to wag.

“Jesus, she’s cute.” He picked her up and put her on Cas’s lap. He didn’t know how to bring up their argument, so he stalled. He didn’t expect Cas to bring his hand to Willow’s snout and begin scratching, and he definitely didn’t expect Cas to smile like he _liked_ her. 

“She is very cute,” Cas agreed. “I didn’t expect Sam to get a pit bull, in all honesty. I was expecting something looked upon as more… wholesome.” He picked up Willow and brought her to his face. She began licking his nose, her back legs kicking in the air in excitement. “I’m glad they picked her, though. Pit bulls get such a bad reputation because their owners mistreat them.”

“Let’s stop fighting.” Something about the sight of Cas and Willow made Dean a little loopy. The words escaped Dean’s mouth before he’d even properly thought them through, but they were out and Dean couldn’t snatch them back.

Cas put Willow down. She started chewing on his thumb. “Were we still fighting?” Cas said mildly. The late spring day made Cas’s eyes look so blue.

“I mean. I just want to clear the air. You weren’t answering your phone. I - I said something stupid and it was...dumb.”

“Stupid and dumb are generally synonyms, you know.”

“You know what I mean.”

Cas just smiled. He seemed at peace there in Sam and Eileen’s backyard, letting a puppy steadily chew off his hand. He could picture Cas in a place like this and hoped Cas would get there one day. 

“I’m sorry,” Dean said again, ducking his head. “I didn’t mean to...I dunno. Make you feel like I didn’t get you.”

Cas shook his head. “I know you accept me, Dean. I was - I’m just tired of a world that makes sex out to be the be-all, end-all of relationships. That’s not my world. I was just frustrated and tired and a little… a little lonely.”

Dean liked pushing Cas, liked pulling reactions from him that made Cas’s color rise, but there was nothing he liked about this. He nudged Cas with an elbow. “You should get a dog. A house. A place like this. The world out there doesn’t deserve you anyway. I’ll join you. I’ve already sworn to be a lifelong bachelor, haven’t I?”

Cas chuckled. “That’s a tempting image,” he murmured. But he didn’t expand. He cleared his throat. “Anyway, how is Charlie?”

“Uh… you sure you want to know?” Dean’s plan to help Charlie was already in full swing, but after getting Cas’s friendship back, he didn’t want to risk losing it again so soon. Or ever, Dean amended.

Cas sighed. Dean almost smiled at how much he missed hearing it. “I have accepted that I cannot control you, Dean Winchester. If you insist on helping Charlie, I am going to stay as close as I can so I can step in if you are about to irrevocably ruin her life.”

Dean laughed. “Good to have you back, Cas.” And it was. 

 

Aaron Bass called that night just like he said he would through his email. Dean wasn’t feeling up to socializing, not after more than a few beers and making up with Cas (welcome, but also emotionally trying) but he’d committed to this mission and he would see it through. He was, however, sleeping in the guest room with Cas in the same bed, so stealth was necessary.

Cas grunted in his sleep when Dean answered with a hushed greeting. 

“Is that Aaron?” Cas asked hoarsely. Dean had told him about the plan, and while Cas hadn’t outright vetoed it, he definitely hadn’t been happy about it. 

“The guy who wouldn’t stop calling you for months?” Cas had asked incredulously, ignoring Willow, who’d been chewing on his shoelaces. “Him? He’s your great plan?”

Half-asleep and half-hidden under his blanket, however, he was much more eloquent: “Tell the creep he can fuck off and let us sleep.”

Dean winced.

“Are you _with_ somebody?” Aaron asked. 

“No!” Dean said, a little too loudly, then, when Cas kicked him in the small of the back, said more softly, “No. Stay.”

Aaron sounded mollified. “Alright. Well. What’s this thing you wanted to talk to me about?”

Cas was still displeased, though he still hadn’t moved from his nest. “Why the fuck is he calling at 1am, Dean? Creep.”

Dean pinched the bridge of his nose. “Listen, Aaron, I was just wondering - I’ve got this friend, and she’s kind of - she’s a good gal, and I wanted her to meet some of my friends, just to - y’know. Expand her circle. I immediately thought of you, of course, because you’re so - so worldly and - and _great._ ” The words sounded cheap on his tongue, and he hoped Aaron wouldn’t catch on.“Her name’s Charlie, and she’s a - “

“Yeah, sounds great,” Aaron said, sounding much more enthusiastic than Dean had been expecting. “Any friend of yours is a friend of mine. You’ll be introducing us? Where do you want me to meet you?”

Dean grinned. He hashed out the details with Aaron and hung up feeling immensely good about himself. He crawled back under the covers with a grin on his face.

“For the record,” Cas said, still sounding at least 23% asleep, “I think Aaron Bass is a horrible choice, and I predict you’ll regret setting this up in some profound way.”

Dean’s smile didn’t waver. “If you say so, grumpy.”

“I do say so. Good night, Dopey.”

Dean was so glad Cas was talking to him again. “Good night, Cas.”

 

He met up with Charlie a few days later at a local Applebee’s. Despite heavily hinting to her that she’d be meeting one of his “good friends,” she was dressed in her usual jeans, sneakers, and nerdy T-Shirt. This particular one read, “What Would Buffy Do?” and had a picture of Sarah Michelle Gellar with her hair in a ponytail. 

“Do you ever wear anything other than merch?” Dean asked, trying not to sound like a douche but still failing.

Charlie’s smile soured a little, but she shrugged. “It’s comfortable, and it gives something for people to talk to me about.”

Dean conceded that fact. “Good point,” he said, and Charlie gave him a bright smile. 

“Merch is how we met, isn’t it?” Charlie pointed out. “My Hermione sticker?”

The details of that night were still fuzzy to Dean, but he definitely remembered thinking about Emma Watson. “Oh, yeah.”

“Anyway, tell me more about this friend of yours,” Charlie said. She’d already ordered a drink and was sipping on it like it was a milkshake, both of her fists pushed up to her face, making her look like a goldfish.

Dean winced. “Stop that,” he reprimanded. “You’re not 10.”

She stuck her tongue out at him but straightened anyway. “So how long have you known him? He cute?” She wiggled her eyebrows at him suggestively.

Dean was satisfied that she was showing some interest. “He’s pretty cute,” he said, though Aaron wasn’t really his type. Only a few people could pull of the scruff, and Aaron was not really one of them. “Scruffy,” he said, watching her reaction.

She nodded encouragingly. “Go on.”

Honestly, Dean didn’t remember that much about him. “Y’know. He’s cool. I hope you like him.”

Charlie’s smile was beatific. “If you like him, I’m sure I’ll like him.”

Damn, Dean was good at this. _In your face, Cas,_ he thought. “Cool,” he said out loud. “He’ll be here soon.”

Aaron came in ten minutes later in a get-up much fancier than Dean had ever associated with an Applebee’s _._ It was obvious he’d taken some time and effort to look good, and Dean appreciated it. When he shook Aaron’s hand, it was with genuine pleasure. “Nice to see you, dude.”

“You too, Dean,” Aaron said, smiling wide. He’d tamed the beard, too, which was a nice surprise. “I’m really glad you contacted me.”

Dean didn’t want to go that far. He merely smiled in response. He sat down and was immediately surprised when Aaron moved to sit next to him in the booth rather than next to Charlie. 

Charlie watched this all with raised eyebrows and a bemused smile. 

Dean cleared his throat once he’d scooted in to let Aaron sit next to him. “Charlie, this is Aaron. Aaron, Charlie.”

The two shook hands politely and exchanged pleasantries.

An awkward silence descended. Charlie’s eyes slid to Dean as if expecting him to lead the conversation. Geez. Was 11am too early for a drink? 

Luckily, Aaron decided to break the silence, though perhaps not in the way Dean wanted him to. “So, Dean, what have you been up to lately?”

Dean balked a little. He had not been expecting to be asked about _his_ life. At the most, he’d expected he would have to smooth away some of the awkwardness that usually came with first dates, maybe fluff Charlie’s feathers a little bit and boost Aaron’s ego, make them look good for the other. 

He floundered a little bit. He hadn’t thought about his life in a while besides to contemplate how good he had it. “Uh. I - uh, same as always, dude. Garage still going strong. Brother got married. Life’s - life’s good. Met Charlie recently, actually, and like I said - “

But Charlie interrupted. She seemed a little confused. “Have you not seen each other in a while?” she asked. “I thought that you were - uh, good friends.”

Dean clenched his fist to avoid slamming a palm into his forehead. 

Aaron spoke hesitantly. “We - we lost touch a few years back.”

Dean almost snorted. Almost. He stifled it. To have “lost touch” was a very gracious way of putting “Dean stopped responding to my messages.” Aaron was an okay guy, Dean supposed, but he was also very, _very_ clingy. The friendship had started out great: Aaron was fun to talk to, great to watch the game with, and didn’t complain about Dean’s music. But then Aaron had started calling _every day_ and wanting to hang out _every day,_ and one day when Aaron called while Dean was driving, Cas had let out a frustrated breath, snagged Dean’s phone from his hand, rolled down the window, and tossed it out without a word. 

“You keep complaining about it but never actually doing anything about it,” Cas had said sullenly, when Dean had demanded _what the fuck, Cas?_ “So there’s your excuse. You lost your phone and you don’t have his number anymore.”

Dean had had to track Aaron down on Facebook to get his number again. 

“But uh, we reconnected recently,” Dean continued, extending an encouraging smile at Charlie and hoping that was the end of the questioning. “And I wanted you guys to meet.”

Aaron nodded. He seemed pleased. “I’ve gotta say, it’s great to meet another one of Dean’s friends. I only ever met Cas, and he was - Dean, I hope you don’t take offense, but he’s not the easiest to talk to. Do you - do you two still hang out?” The last few words were tentative.

Dean bit back a smart remark. He dragged his palms down his denim-clad thighs and tried not to clench them into fists. “Yeah,” he said, “Yeah, all the time.”

“Ah.”

“He seemed easy enough to talk to, to me,” Charlie said. 

“Maybe he’s loosened up,” Aaron said noncommittally. “Anyhow, Charlie, uh, tell me about yourself.”

_Oh, thank God,_ Dean thought, almost rolling his eyes in relief. He was starting to remember why he hadn’t been _that_ upset with Cas for getting rid of his phone. He checked the time. 

Twenty minutes later, Dean’s phone rang. He answered it quickly, relieved; both Aaron and Charlie seemed to be intent on asking him questions rather than getting to know each other, and the sooner he was out of there the better. 

Cas was on the other line, as they had planned. “It’s an emergency,” Cas said blandly. “Oh, no. Whatever will we do? Willow has gotten out of the house. She has gone missing. Oh, no.”

“What?” Dean said, with considerably more emotion than Cas. “Since when? Okay. Okay, I’ll be right there.” He ended the call. “I’m so sorry, you guys - I gotta go help Sammy. Willow’s gotten out of the house and they can’t find her.”

“Willow?” Aaron asked, brow furrowing. Dean didn’t really want to explain any more, but at least Aaron was getting up so that Dean could shuffle out of the booth.

“My brother got a dog,” Dean explained. “Look, uh, can I catch up with you guys later? Maybe? I don’t know how long this will take. But take your time, alright? I’m sure you guys can find something in common.” He waved distractedly at them, then looked at his phone in concern for good measure. “I hope she’s all right,” he mumbled, then, frowning, said, “I’ll see you guys later.”

He walked out of the restaurant and left Charlie and Aaron staring after him. 

 

He called Cas when he got home. “Couldn’t have injected a _little_ more enthusiasm into that scene, Cas?”

“You may remember that I am not exactly a fan of your plan, so forgive me if I wasn’t as enthused as you might have preferred.”

“Whatever, man,” Dean said, pulling a beer out of his fridge. Now that his Sunday was free, he was going to spend it on his couch with a beer balanced on his stomach. “At least it worked.”

“Mm,” Cas said. 

Dean paused. He pulled the phone away from his ear to make sure the call was still connected. “Still there, Cas?”

“Uhuh,” Cas said.

“You busy or something?”

“Not particularly.”

“Okay,” Dean said, settling on his couch and groping for the TV remote. “You, uh - wanna tell me why you’re so quiet?”

There was a long pause. 

Dean left the remote where it was and sat up straighter on the couch, nestling the phone more securely against his ear. “Dude, you’re freaking me out here,” he said.

Cas finally sighed. “I don’t know how you’re going to react to this,” he said slowly. “But I have to tell you something.”

Dean let out a short laugh, a little nervous. “You’re not pregnant, are you?”

Cas was silent. Dean imagined him closing his eyes and shaking his head at the ceiling of his apartment, waiting for Dean to be ready to listen.

Dean shook his head, pressed his eyes shut tight. “Alright. What is it? You okay?”

“I’m fine,” Cas said softly. “I just - I ran into Daphne earlier.”

Daphne. _Daphne._ Cas’s ex from two years ago. The relationship had been Cas’s only real serious relationship, and it had ended only because she had moved away to be closer to her ailing parents. A bolt of cold dug into Dean’s stomach. It wasn’t that he disliked Daphne - no, she’d been sweet and kind and understanding - but she’d also left Cas in the most pain Dean had ever seen him in. “That’s. That’s something.”

“I… invited her and her friend to your mom’s place this weekend.”

Dean imagined Daphne and Cas standing together in the cool air of Mary Winchester’s cheery backyard. It wasn’t hard to do because it had been a common enough sight a few years ago. Still, Dean wasn’t comfortable knowing that the woman who had caused his best friend the biggest heartbreak of his life would be coming to Dean’s mom’s house like she was a _friend._

“Mary knows, and she’s fine with it,” Cas said. “I just need to know if you’re okay with it.”

Dean bit down on a knuckle. It would be so easy to tell Cas no. So easy. Daphne had no place in their lives anymore, he wanted to say. But he remembered the week he had just spent not speaking to Cas, and imagined another week just the same. And another and another. He couldn’t risk losing Cas again. “Dude, of course,” Dean said, though the five seconds it took him to answer Cas might not have helped his case. “If you want her to come, and my mom’s okay with it - sure, why not? And her friend too. She can bring her friend. All her friends. Just - yeah, all of them.”

“Dean.” Cas didn’t sound convinced. “Are you sure?”

Dean shook his head. Bit down on his knuckle again. _No._ “Yeah.”

 

Mary’s house had three bedrooms - two of them now long empty. It was partly because her house was so empty that she insisted on a family dinner once every month. Dean and Sam and Eileen and Cas and Bobby were usually the only ones to come by. This month, however, there were four extra guests, because not only had Cas invited Daphne and her friend, Dean had also decided that Charlie and Aaron should be welcomed as well. He told himself it was not out of spite, but he knew that just because he said so didn’t make it true. At any rate, he reasoned, it was probably better for everyone if he had something to distract him from Daphne and Cas.

He arrived with Charlie and Aaron in tow. He’d called ahead to let Mary know, but even so, when she opened her front door, her smile was a little brittle. She liked Charlie enough, but she’d heard enough about Aaron from Cas to be a little defensive. “Come in,” she said. “We have… more guests than usual this month. It’ll be… great.”

Charlie and Dean exchanged winces and followed her out into the backyard, where a folding table had been set up for the food. Charlie immediately went to greet Eileen (and Willow), leaving Aaron and Dean by the food.

“I can’t believe I never met your family,” Aaron said. He was eating chips straight from the bowl. 

Dean had already seen that Cas and Daphne hadn’t arrived yet. Good. “Yeah,” Dean mumbled. “You want a beer?”

“I’ll get it, man,” Aaron said, going past Dean toward the cooler.

The cooler was right behind Dean, so it’s not like it was much trouble, but Dean was too preoccupied with his thoughts to care. 

“What are you, too cool to come and greet me?”

Dean turned. To his side was Bobby: scruffy and surly and donning his usual baseball cap. “Bobby, hey,” Dean said, leaning in for a hug. “Sorry. Things have been busy; I’m a little distracted.”

“You’re working too hard,” Bobby said. He clicked a tongue. “Never thought I’d say that.”

Aaron cleared his throat. He was holding out a beer each for Dean and Bobby. “Hi,” he said.

Bobby surveyed him with a narrow look, but he took the beer all the same. “You’re new.”

“This is Aaron,” Dean said, feeling a little self-conscious. “Friend of mine and Charlie’s.”

“Charlie’s the redhead, then?”

“Yup.” 

Bobby nodded, if a little begrudgingly. “She seems like a good enough sort.”

Charlie was rocking Willow in her arms while chatting with Sam, probably something to do with rescue dogs.

“Not so sure about you yet,” Bobby continued, looking at Aaron.

“Jesus, Bobby,” Dean muttered.

But Bobby was already walking away to help Mary with the rest of the dishes.

An awkward silence descended. 

Dean blew out an embarrassed breath. “Sorry about him. He’s - “

But Aaron was holding up a hand. “Nah, don’t worry about it. I get it. New guy. Meeting the family. Always gonna be awkward, right?”

That was a strange way of putting it. “...yeah. Uh, anyway, you think Charlie needs a drink? Maybe you should get her one.”

Aaron nodded. “Yeah, that’s a good idea.” 

Dean let out the sigh he’d been holding only when Aaron traipsed off to hand Charlie a beer. Then Mary’s back door opened and Dean had to clench his fist to keep from scowling at the sight of Daphne in her usual sensible shoes stepping softly into the backyard. An unfamiliar woman followed her, looking about the backyard with a soft, pleasant smile on her face. Cas followed, then Mary, who had a dark look on her face. 

Cas led Daphne and her friend to Sam first, probably guessing (correctly) that Dean needed a little time to calm down before greeting his ex. Mary joined him.

“So,” she said.

“So.”

“You think he wants to get back together with her?” Mary knew Dean’s feelings toward the situation because they were exactly the same as hers. 

Dean took a long, long draft of his beer as he watched Daphne reacquaint herself with the people she’d almost called family two years ago. “I dunno, mom,” he said. “I just hope he knows what he’s doing.”

“Is she in town long?”

Dean hadn’t asked on the phone with Cas; he’d been too eager to disconnect the call and lay in bed and _not think_ anymore. “No idea. Don’t even know if her folks are still around. Didn’t ask. Didn’t want to.”

“She’s a good enough lady,” Mary said evenly, “But if she hurts that boy of mine again, I’ll chase her off with a shotgun myself.”

That made Dean laugh. He kissed his mom on the temple, more to keep himself from looking at Cas’s hand, hovering ever so lightly on Daphne’s back. “I’ll join you.”

“Anyway,” Mary said, “What’s going on with you and Aaron?”

“What do you mean?” Dean asked. He’d finished his beer already and wanted another one, but he wasn’t about to dig through the cooler with his mom right there.

“I mean it seems like he’s into you,” Mary said, arching an eyebrow.

“What? No. He’s here for Charlie.”

“Oh,” was Mary’s only reply. 

“You know that other lady’s name?” Dean asked, remembering that there was another new face in the backyard. 

Mary furrowed her brow. “I don’t think I was listening very much when we were introduced. It started with a G, I think. Glinda? Gladys? Why?” Mary said, sending a cheeky smile her son’s way. “She’s cute, isn’t she?”

She was. She was tall with big eyes and curls in the brown hair she kept swept back from her face. There was something otherworldly about her, something that reminded Dean of Cas. She made eye contact with him as he was watching her, and the smile that spread across her face was friendly and sincere. He’d half been expecting something predatory to come across her face, but her face remained open and happy. 

“Well,” Dean said, making up his mind, “Gotta bite the bullet sometime, right?” And he marched right up to the crowd.

“Hey, Dean!” Sam said. He was holding an exhausted pit bull puppy in his arms. He made room for Dean right next to him. “We were about to call you over.”

Dean pasted a smile on his face. “What’s going on?”

“Dean,” Daphne said, with so much emotion Dean was afraid she might dislocate something. She reached across the circle to take one of his hands between both of her own. “It’s so nice to see you.”

Dean did not doubt that she meant it, because that was the kind of person she was. “Hey, Daphne,” he said. “You uh - you in town long?”

She smiled. “I’m not sure,” she said. “My parents’ health improved, so I’m taking a bit of ‘me time’ while I can. I’m staying with my friend Gilda for the time being. We just learned she lives just down the street from Sam.”

Dean’s thoughts were being pulled in every direction. He struggled to stay with the conversation, though his head was running through the number of possibilities of running into Daphne if he visited Sam any time soon. 

Daphne ushered Gilda forward, and Gilda extended a long, graceful hand toward Dean. Dean took it. She really was a beautiful woman. “Nice to meet you,” Dean said, and it was a genuine statement.

“You too,” she said, and even her voice was smooth and angelic.

Aaron cleared his throat. He seemed a little disgruntled, but that wasn’t Dean’s problem. “We should all go out sometime,” Aaron said, looking around at the circle. He was smiling, but it seemed a little hard around the edges. “Get to know each other. I’d love to get to know Dean’s family a little bit more.”

Sam nudged Dean with an elbow. Dean pushed back.

Eileen smiled widely. “I’m in,” she said. 

Charlie had been quiet, but she was suddenly animated once more. “If all of us are going, I’m definitely in too.”

Daphne looked at Cas. Cas looked at Dean. Dean looked at his shoes.

“Sounds like a great idea,” Cas said.

Cas called later that night, after Dean had dropped Charlie and Aaron off at one of his favorite bars. They’d begged him to come with, but he’d been exhausted, so he’d let them off and driven home, wanting nothing more than to dig through his fridge and see if there was a stray bottle of beer he hadn’t seen.

But then Cas called, almost as soon as Dean had taken his shoes off. “Hello?” 

“Hello, Dean.”

Dean suddenly wanted to crawl into bed and pull the covers over his head. He definitely didn’t want to talk to Cas. “Hey.”

“Did you… want to talk? I know you’re not completely on board with… Daphne and me.”

“Daphne and you,” Dean said, trying the words out on his tongue. “Daphne and - so you _are_ getting back together.”

There was a long, long pause. “I’m not sure, Dean.”

“But you’ve talked about it?”

“Not in so many words, no.”

Dean really didn’t want to be having this conversation, though he wasn’t quite sure why. He could help Cas. He could see Cas through this. Cas could be happy if Dean helped him. But if Cas being happy meant being with Daphne? That was something entirely different.

“Cas, if she hasn’t brought it up - just, don’t take this the wrong way, alright? I just don’t want you to get your hopes up. She - she hurt you badly, man.”

“She had to leave,” Cas said quickly, almost like he’d been waiting to defend her, or almost like he’d been repeating it himself the whole night. “She didn’t mean to.”

“And she might leave again,” Dean said. “She said it herself: she doesn’t know how long she’ll be in town.”

Cas was quiet, and Dean suddenly remembered the conversation he’d had with Cas only a few short weeks ago, after they’d made up. _I was lonely,_ Cas had said.

“Don’t do it just because you’re lonely, Cas,” Dean said. He sounded like he was begging, and he supposed he was. “That’s - that won’t end well for anybody. Not for you, not for her, not for me.”

“Not for you?” Cas repeated dryly.

Dean smiled, if only because Cas was beginning to sound like himself again. “You think I like when you’re moping around?”

Cas sighed over the line. “Very well,” he said. “I’ll think about what you said. But I am still taking her with me when we go out next week.”

“Don’t remind me,” Dean groaned. “Dumb idea. If Aaron wanted to spend time with Charlie, he should just _ask_ her.”

“You could just...not go.”

“What, and miss Gilda?”

“Oh. She is pretty, I suppose.”

“I wouldn’t mind getting to know her,” Dean said. “Lifelong bachelor I may be, but I gotta have _some_ fun, right?”

“If you say so, Dopey.”

“Shut up, Grumpy. Go to sleep.”

“Good night, Dean.”

“G’night, Cas.”

 

The week passed by quickly. Dean’s restoration shop maintained a constant flow of customers, and on Wednesday he even had to ask (beg) Bobby to come in to help ease the strain on his mechanics, despite having also donned his old pair of coveralls for a shift. The work felt good for him, and it succeeded in distracting him from the utter bullshit it was that Cas was actually considering a return to Daphne. 

Still, by the time Friday rolled around and Dean was scowling at his closet trying to decide what to wear for the semi-fancy “lounge” Aaron had picked out, he had managed to drum up a level of irritation that made even seeing Sammy and Eileen seem like a chore. If he hadn’t already told Cas he was going, he wouldn’t have bothered to show up.

The lounge was half an hour away, and two blocks from Dean’s bar of choice. He’d 

passed by the place dozens of times but had never paid it much attention, mostly because the crowd that seemed to gravitate toward the glass double-doors was made up of college kids and twenty-somethings, and while Dean liked to think he wasn’t _old,_ he definitely wasn’t twenty-something anymore either. Going in made him feel skeevy, and indeed, a few girls who looked barely legal to be drinking started whispering behind their manicured hands as they passed by. Dean knew he should have stayed home.

His party was tucked into a dark corner which, while he was thankful not to be in the middle of the room, did not make him feel like any less of a creep. The semicircular booth they were squeezed into was at least cool. Dean took the space next to Sam rather than Cas and ignored the stare that Cas sent him over the table between them. Daphne was sitting next to him and Dean couldn’t - he just couldn’t look at them.

He picked up the menu in front of him. It was sticky. Dean winced both at the stickiness and at the contents of the menu; what was wrong with a plain whiskey, and why did people insist on sticking herbs in everything?

He hadn’t bothered greeting anybody. His first words were to a passing bartender. Sam was staring at his profile.

“What?” 

“You good?” Sam said lowly. 

Dean bristled. “I’m great, Sammy. I just need a fucking drink that doesn’t have something green floating in it.”

A hand on his arm startled him. He looked toward the newcomer and felt both his eyebrows and heart rate rise. 

“Gilda,” he said, a little breathlessly. She was holding a drink. It was pink. There was a sprig of mint floating on top of the ice. He almost didn’t mind it because it matched the red dress she was wearing. 

She smiled at him in greeting and sat next to Cas. “It’s nice to see you made it,” she said, taking a dainty sip of whatever godforsaken concoction she ordered.

Dean smiled at her helplessly. 

Sam snorted inelegantly next to him.

 

The booth was not conducive for socializing - not the kind of socializing Dean wanted, anyway, because while Sam would have been glad to talk Dean’s ear off about his practice, Dean was determined to get Gilda alone (or as far away from Cas as possible, because there was something that rubbed him the wrong way about chatting a girl up with Cas _right there_ staring at him _._ ) So eventually, after downing his first glass of whiskey and seeing that Gilda had more or less finished her drink off as well, he caught her eye and nodded toward the bar. 

She stared at him with a contemplative smile on her face for a long beat, then she was nodding, and Dean was trailing after her toward the bar. He could feel eyes on the back of his head. Cas? Sam? Charlie? Everyone? Who knew? But Dean was going to try his damnedest to get something out of this night, especially if Cas - 

Dean shoved the thought of Cas from his head. Dean didn’t need to be cockblocked by his own irritable thoughts. Gilda turned toward him when she reached the bar and smiled. The smile reached her eyes. Not for the first time, Dean was struck by the otherworldly quality she had about her, like she’d been born among the stars and found everything about earth infinitely curious.

“This place is nice,” she said. She sounded like she actually believed what she was saying. 

“It’s something, alright,” Dean said, then signaled a bartender.

Gilda was still smiling at him when he looked back at her. “You don’t enjoy this place?”

“It’s not really my scene,” Dean hedged, then ordered another whiskey. “You want another drink?”

Gilda asked for a specialty cocktail. Dean did not doubt it would turn out to be a primary color. 

“How long have you known Castiel?” Gilda asked, after a small pause. 

Dean could feel his smile grow a little brittle, but he cleared his throat and thought back. “Uh - 15, 16 years? I was a senior in high school, finally moved back in with my mom and found a high school that would accept my credits. Cas was one of the few people who wanted to talk to me.”

“I find that difficult to believe,” Gilda said. She kept smiling like she knew the secrets of the universe. “You seem to be a very kind person.”

This was definitely not how Dean’s usual conversations at a bar went. Compliments usually centered around his hair or his smile or his muscles, not his kindness. His mom, Dean suddenly thought, would love Gilda. He scratched the back of his neck. “Not back then I wasn’t. Angry at the world, stubborn, had a problem with authority. Almost got kicked out about half a dozen times. Cas didn’t care, though. Helped me study, didn’t leave when I lost my temper.”

“A good friend, then,” Gilda concluded. 

“An understatement,” Dean said, then exchanged a few bills for the two drinks the bartender slid toward them.

Gilda’s drink was blue. She sipped it and smiled again. “Thank you.”

“No problem.”

 

Ten minutes later and Dean was struggling to counter all of Gilda’s smiles. Everything she said was laced with sincerity, and while Dean could tell she was genuinely pleased to be spending time with him, he was equally convinced that she would be pleased to be spending time with literally anyone in the world. He liked her. But he didn’t _like_ her. And his face was starting to hurt from smiling back at her.

When Aaron made his way over to them, Dean was almost glad, though he was a little irritated to see that Charlie hadn’t followed.

“Hey,” he greeted.

Aaron situated himself between them and flagged down a bartender. “Hey,” he said.

“Are you enjoying yourself?” Gilda asked, and she finally turned that smile on someone else. Dean massaged his jaw discreetly.

Aaron was staring at her like she was an alien. Dean knew the feeling.

“Yeah, I guess,” Aaron finally said. “I’ll have whatever he’s having,” he then said to the bartender. “Dean, you want another one?”

“I’m driving.”

“Oh, yeah, I meant to ask - you cool dropping me home?” Aaron’s stare was a little off-putting.

Dean blinked. “Sure.”

“Cool.”

“How’s Charlie?” Dean asked, watching Aaron’s face.

Aaron shrugged. “Seemed okay. Eileen was showing her a video of the dog.”

Gilda reached across Aaron to touch Dean on the arm. “Dean,” she said, “Thank you for the drink. I’ll see you both later.”

Both Aaron and Dean watched her walk away. 

“Thought I’d come over and rescue you,” Aaron said, winking. “She’s a peculiar one.”

An inkling of a suspicion started tapping at the inside of Dean’s skull. Carefully, he said, “I dunno; I like her.”

Aaron gave him a strange look. He said nothing else for a while.

 

Dean did not say goodbye to Cas or Daphne, but neither did he say goodbye to his brother and sister-in-law, so he figured Cas would understand. Aaron, however, insisted on saying goodbye, presumably to Charlie, so Dean went outside to start the car. He programmed his GPS to Aaron’s place. Seeing Aaron’s address stored in his phone already, however, had Dean beginning to feel a little bit cramped.

“You have a car, don’t you?” Dean asked, once Aaron had slid into the front seat.

Aaron gave Dean a curious look. “Yeah, why?”

“Just wondering why you don’t take it,” Dean said, maybe a little too gruffly, because Aaron looked at him with a frown.

“Oh,” Aaron said. “I thought you preferred we take your car. We can start taking mine, if you want. I don’t mind.” He started humming along to the track playing through the stereo and looked out the window.

As Dean pulled out into traffic, he tried to puzzle out what bothered him about Aaron’s answer. It was phrased strangely, somehow, like Aaron had run the sentences through a series of languages on Google Translate and then turned it back into English. The reply had made perfect sense, but something about it wasn’t quite right. 

Halfway to Aaron’s apartment, coasting along a freeway, Dean suddenly understood. _We,_ Aaron had said. _We,_ as in Aaron and Dean taking one car when they really should have been taking two separate cars this whole time. _We._

“Jesus,” Dean said out loud.

“What was that?”

“N-nothing.” Oh, but if what Dean suspected was true, it was most definitely something.

He spent the rest of the ride wondering how to bring up his suspicions without offending Aaron. By the time he pulled up in front of Aaron’s apartment, however, mortification had sealed his lips shut.

But then Aaron fidgeted in the front seat instead of reaching for the car door. “Listen, Dean,” he said. “I gotta say something.” 

Dean didn’t say anything. He stared.

“I know you’re naturally a friendly guy, so maybe what you and Gilda were doing was completely innocent. But uh - I think you should know that it was a little upsetting to see you and her talking like that. I know we haven’t established - “

“I’m not friendly.” It was the first thing Dean thought of to say to stop Aaron from going any further. 

Aaron paused. “What?”

Dean groped about for something, _anything,_ that would stop this conversation, because if what Dean was suspecting was true, Aaron was about to talk about _them,_ about the _we_ that he had referred to earlier, as if Dean and Aaron were… a couple. God, Dean was an idiot. “I’m not friendly. I was flirting with her.” And God, Dean was a _dick._

Aaron recoiled a little bit. “Sorry?”

“Okay. Uh. I think there may have been a misunderstanding somewhere along the line here.”

Aaron opened his mouth. Closed it. “I’ll say,” he said.

“I’m… not interested.”

Aaron opened his mouth. Closed it. Opened it again. “I don’t understand,” he said, laughing a little bit. Disbelieving. “You - you messaged me and introduced me to your friends - “

“That doesn’t mean I’m interested - “

“I met your _mom_ \- “

Dean shook his head. He felt a little frantic. Jesus, how could he have fucked up _this badly_? “Listen to me, dude. I - All I wanted was for you to meet my friend Charlie. I was trying - I was trying to set you two up.”

Aaron stared at him. His jaw hung open. Long moments passed. Finally Aaron put a hand on a door handle. “I’m gay,” he said, “And Charlie? She’s… you know what? I’ll let you figure that out on your own.” He opened the door and climbed out. Then he turned around and bent down to say one last thing: “Don’t contact me ever again.” He slammed the door.

 

Dean didn’t know who else to call. He couldn’t call Charlie - that was a conversation he needed to have in the daylight, with plenty of witnesses around in case she decided Dean’s life was forfeit for trying to set her up with a gay man who was interested only in Dean - and it was past midnight, so Sam was most likely asleep. Cas was the last choice, and really, Dean’s _only_ choice, because despite knowing Cas would probably be a smug bastard, Cas would also know what to say to make Dean feel at least a little bit better.

Cas’s voice was rough when he answered, but just the fact that he answered warmed Dean’s heart. “Hey,” Dean said.

“Dean,” Cas said neutrally, “Are you talking to me now?”

Oh, yeah. “Shit,” Dean said faintly. “Dammit. Cas. I’m sorry.”

“You spend the whole night ignoring me, you don’t say bye, you don’t text to say you got home safely, then you call me at - 2:09am? Really, Dean?”

“I’m home,” Dean tried feebly. When Cas didn’t respond, he groaned. “I’m sorry, alright? I don’t know how to act around Daphne!”

“I’m not Daphne, if you hadn’t noticed, Dean. You know how to act around _me_.”

“But you’re _with_ her,” Dean said, and even to his own ears, he sounded jealous. 

There was a long pause. Dean, having lain awake for two hours trying to figure out what the fuck he was going to do, was sitting up in bed with the covers pulled up to his waist. He imagined Cas was doing the same, maybe in those stupid bee pajamas Dean had bought him as a joke. “Will my being with Daphne be a problem, Dean?” Cas finally asked. It was said so quietly that Dean barely made it out.

“Are you actually with her, then?”

“No,” Cas said, and Dean felt the vice grip around his heart loosen. “But I want to know. If it does happen - “

This conversation was just making Dean feel worse. He pulled the covers over his head and closed his eyes. The answer, Dean knew, was _yes_. _Yes,_ Cas being with Daphne would be a problem with Dean. Dean would spend every day wondering when Daphne would have to leave again, when Cas would fall apart again. He might never be able to trust Daphne, and _yes,_ that was a problem for Dean. But he knew the answer Cas wanted to hear. But he’d never been able to lie to Cas, not with any success. “I don’t know,” he finally admitted. Then, truthfully, he said, “But I’ll try to be okay with it. If it happens.” _Please don’t let it happen_ , Dean thought desperately.

“If it happens,” Cas agreed. “Thank you.”

Dean pinched the bridge of his nose, feeling a migraine building right between his eyes. 

“Why did you call?” Cas asked.

“Shit,” Dean said, recalling the rest of the night. His migraine throbbed when he laughed bitterly at himself.

“Oh, Dean,” Cas sighed. “What happened?”

“Aaron. Aaron happened.” 

There was a note of derision in Cas’s voice. “Of course.”

“No, Cas, _I fucked up,_ and Charlie’s going to hate me.”

“Charlie adores you,” Cas said calmly, “despite my best efforts to warn her away from your idiocy. It would take a lot to get her to hate you.”

Dean didn’t even bother arguing with the “idiocy” part because honestly, that part was true. “Aaron thought we were dating. Him and me. Dating. How big of an idiot does that make me, Cas?”

“A - a rather large one,” Cas replied, but his voice was unsteady in his surprise. “That’s… quite a mistake.”

“Ya think?” Dean said. “Charlie trusted me.”

“We should have seen this coming,” Cas sighed. “He was always attracted to you, but neither of us wanted to see it.”

“Why did I even pick him?” Dean asked. “What kind of friend am I to pick _this guy_ for Charlie?”

“To be fair, Dean, you don’t have many friends.”

“What, and you’re Mr. Social?”

“No, but I’m not stalking girls at weddings and setting them up with my friends.”

Dean wanted to run into a wall repeatedly until he knocked himself out. “Jesus, what was I thinking?”

“Do you really want to know?”

“I really do.” The details of Sam’s wedding were alcohol-fuzzy.

“I think you wanted to prove to me that you were good at matchmaking.”

“Oh, God, never mind. I take it back; I don’t want to know, you self-righteous dick.”

But Cas continued. There was a note of amusement in his voice. “And I think we have an abundance of evidence that suggests that you are definitely _not_ good at matchmaking.”

“Okay, well, _that’s_ yet to be seen, alright?”

“Dean, please do not tell me you’re still going to subject Charlie to your experiments. Have you told her about Aaron?”

Dean pressed his lips together. “It’s past midnight, Cas, c’mon, you think I’m gonna wake her up for that?”

“So that’s a no.”

“Whatever,” Dean said gruffly. “I get it - I’ll cool it for a while if it makes you feel better.”

“Infinitely,” Cas said, and he really did sound relieved, much to Dean’s irritation. “Now can I go back to sleep, or do you have any other problems to bring to my attention?”

“Oh, shut up.”

 

He put off meeting Charlie for a few days. In the meantime, Aaron blocked him on social media, and the few times Dean tried to call him to clear the air, Aaron picked up just to hang up on him. Dean really couldn’t blame him. While Dean’s romantic history was decidedly more casual than most, he could still imagine how it must hurt to be led on, even if the person doing the leading-on had no idea.

A few days after, as Dean was sitting in his quiet living room staring at his phone trying to decide if he should call Charlie or not, her contact information lit up the display. _Can I call you?_ the message read. That was certainly ominous.

Dean got up to grab a beer. Then he shot off a reply: _Sure._

When Charlie called, Dean had already chugged half of his drink in a preemptive maneuver to make the coming conversation a little easier. 

“Hey,” Charlie said. She sounded puzzled.

“What’s up?”

“Have you heard from Aaron lately?” she asked. “We were supposed to binge _Peggy Carter_ this weekend but he hasn’t been answering my messages. I think he blocked me on social media, too. Do I - uh, need to know anything?”

Dean closed his eyes. “Yeah, uh. Look, Charlie, I’m sorry. It’s - it’s not gonna work out with Aaron.”

“Oh?”

“He - he misunderstood a few things about the situation.” He couldn’t tell her the whole truth. It may have made him a coward, but he wasn’t going to tell her exactly what Aaron had misunderstood, wasn’t going to tell her that Aaron’s feelings were for _Dean,_ and not her. He hoped she wouldn’t press.

There was a long silence on the end of the line. Then, “Okay. It would have been nice to hear from him himself, but I understand.”

Dean paused. “You - you do?”

“Yeah,” Charlie said. She sounded almost cheerful. “Sometimes things don’t work out, right? I didn’t think he was a good fit myself.”

Dean massaged a temple and tried to reconcile Charlie’s reaction with the situation. “So you’re - you’re gonna be okay.”

“Uh, yeah?” Then, tentatively, she asked, “Will _you_ be okay?”

“He’s not answering my calls, but yeah, it’s not a big deal.”

“Great,” Charlie said. “Only thing is I need someone to watch _Peggy Carter_ with me this weekend. You wanna come over? Might cheer us up.”

“I dunno, Charlie,” Dean replied. “I’ve been letting work stack up at the shop, might have to work all weekend.” In reality, Dean didn’t feel right being the one to comfort Charlie, not when he was at fault for her disappointment. Plus, he’d promised Cas he’d step back and take stock of his actions, so he was going to take the weekend to do that.

“Damn. Alright. You think, uh, Gilda might be free? I don’t want to interrupt the newlyweds.”

For the first time since the conversation started, Dean felt a smile tug at his lips. Gilda would be perfect for cheering Charlie up. “Sweetheart, that’s a great choice. Let me get you her number.”

 

Dean’s mom insisted on moving the next family get-together to a local park, even though Dean told her they would be at least one guest down, since Aaron wouldn’t be attending. “Well, good riddance,” she said over the phone. Dean had just pulled into his driveway. “He asked me for my apple pie recipe the last time, and I had to make one up on the spot. How many apples do you think you need for a pie? I told him he needed two dozen.”

Dean chuckled imagining the look on Aaron’s face. “Y’know, you could have told him where it was actually from.”

“And make you look bad? Honey, I would never do that in front of a boyfriend.”

The smile on Dean’s face turned into a wince. “He - Mom, I brought him so I could set him up with Charlie. I was never interested in him.”

“But he was interested in you, wasn’t he?”

Dean stifled a sigh. He didn’t answer.

“Hah! Knew it. A mother always knows.”

He opened his car door and climbed out. “You know anything else I don’t? Feel like I’ve been off my game lately.”

“Oh, honey,” his mom said. “I know a lot of things you don’t, but I’m not sure you’re ready to hear them.”

One of Dean’s front steps was creaking. He turned around and put his weight on the step again and frowned when the wood bowed. “What are you talking about, mom?”

“About Cas.”

Dean looked up from the step, brows furrowing. Fred from across the street waved at him. Dean lifted a hand automatically, but his head was elsewhere. “About Cas,” he repeated. “What about him?” He would feel his ears getting hot in anger toward Daphne, even though he knew he shouldn’t jump to conclusions.

Mary hummed contemplatively. “I think I’ve said too much already.”

“About him and Daphne?”

But Mary was determined not to answer. “So I’ll see you next week Saturday, right? We’ll make it a potluck, maybe grill some hot dogs.”

“Mom.”

“It’ll be a nice change. Maybe you and Sam could throw around a football again.”

“ _Mom_.”

“Make sure you lock up tonight, honey. And eat well, please! Love you!” 

The call ended. Dean stared at the display until it winked out and all it was was a hunk of metal sitting in his palm. He pocketed it and turned to his door, keys in hand, trying to quell the frustration of unanswered questions. Maybe he should call his mom back. Or maybe he should call Cas and see if anything had changed between him and Daphne since Dean had last called. 

He shed his jacket once he got inside, then pulled his phone from his back pocket. Cas was #1 on speed dial, so it was just a matter of tapping the 1 and pressing the call button. But Dean’s finger paused before it made contact with the screen. 

He couldn’t do it. He wouldn’t do it. He’d told Cas he’d try to be okay with him and Daphne, and if Dean couldn’t keep it together after one inconclusive comment from his own mom, he didn’t deserve to be called Cas’s best friend.

He called Charlie instead.

“Hello,” she answered. She sounded happy to hear from him. Dean settled on the couch cushions without removing his shoes and closed his eyes, content just to hear a friend’s voice.

“Hey,” he said. “What are you doing?”

“Just chilling. Chatting with my friends. You know how I do.”

“You wanna catch a movie?”

A pause. “I have company coming over in a bit, actually…”

Dean felt a smile tug at his mouth. “‘Company,’ eh? You’ve been busy. Who is it?”

Charlie sounded pleased but embarrassed when she said, “Just a friend for now. I dunno if it’s actually gonna go anywhere. We’re kind of in the weird is-this-a-date-or-just-two-friends-hanging-out kinda phase.”

“Well, alright,” Dean said, not bothering to hide a long sigh. “Guess I’m gonna have to hang out with Sammy. Good luck, though.”

“I’m sorry! Say hi to Willow for me!”

Dean promised he would and bid her goodbye. He hadn’t planned on doing much tonight - maybe catch up on the scores and hit the sack early - but after his conversation with his mom, he was sure he’d be too restless to do either of those.

He called Sam. “Hey, Dean,” Sam said. He sounded exhausted.

“Hey, dude. You okay?”

“The puppy’s sick. Eileen had some bad takeout and Willow must have gotten into it from the trash. Just got back from the vet and they’re gonna keep her overnight just to watch her.”

“Damn, little bro. Married life, eh?”

Sam groaned. It sounded muffled, like he’d put a pillow over his face or faceplanted into his mattress.

“You need anything? I’m not doing anything; I can drop off some food or some drugs or something.”

“Nah,” Sam said. “Did a grocery run already, so I think we’re good. Thanks, though.”

Dean stamped down the seed of disappointment that had just begun to sprout. “‘Course, man. I’ll see you soon. Take care of my sister, alright?”

“Always,” Sam said. “See ya.”

The call ended. Dean closed his eyes and wondered what it might be like to be needed by somebody.

 

No one besides his mom called him over the next two weeks. He received a few messages from Charlie and Sam, and one preoccupied voicemail from Cas, but Dean’s afternoons and evenings were spent browsing through Netflix unsuccessfully. He toyed around with the idea of calling Gilda once or twice, but just thinking about smiling gave him a migraine, so his phone stayed on the coffee table. 

The calls with his mom were perfunctory, and he didn’t dare bring up the Cas comment she had made because, he reasoned, Cas had given Dean no reason to worry about him and Daphne. Unless Cas’s radio silence counted as reason to worry. Was it reason to worry? Dean couldn’t decide.

Eventually Dean decided to go the safe route. The night before their family picnic, he sent a text to his best friend: _Getting the drinks ready for tomorrow. Daphne and Gilda coming?_

All Cas said was _yes._

No sarcastic reply, no inquiry after Dean’s health, nothing besides one word. _Nice to hear from you too,_ Dean sent, and though he immediately regretted it after he sent it, there was a vicious part of him that wanted Cas to know that Dean was upset.

He waited and waited for Cas to reply, but he never did.

 

Dean arrived at the park in a sour mood. Usually his visits with family were something to look forward to, something to lighten his mood after a long work week, but the last one had only put him in a worse mood, and this one was already starting off on the wrong foot thanks to Cas’s radio silence. Dean would almost have preferred if Cas didn’t show up, but Cas’s car was already parked when Dean started lugging out the cooler from his trunk.

The walk to the area they’d agreed to meet was barely a walk - within five minutes, dragging the cooler behind him, he spotted Sam with Willow on a leash. Mary and Bobby were in chairs in the shade, and Cas was manning the grill, though it seemed he was having trouble starting it up. Charlie had made her own way there and was, to Dean’s slight sense of betrayal, laughing at a joke that Daphne made. Gilda was sitting on a tree root in a flowy sundress that showed off her tan shoulders.

Dean hitched on a grin for his mom and Bobby when they caught sight of him. 

“Feels like it’s been a while, boy,” Bobby said, looking at him through critical eyes. “You lose weight? You seem tense.”

Dean’s smile felt like concrete: cold and immovable. “Shop’s been getting busy and all; not much sleep.”

Mary sighed and Dean ducked down to let her kiss him on the forehead. “Honey, you need to take care of yourself.”

“I’m fine, mom,” Dean said. “Can’t stop success.”

When he straightened, Sam dumped Willow into his arms. “Uncle Dean missed you,” Sam said, clapping Dean on the back. “Will you hold her? Gotta go help Eileen with the food.” Without waiting for an answer, Sam skipped off to where Eileen was approaching with a dish in her hands.

Willow licked Dean’s chin. “Your mommy’s keeping your daddy busy, isn’t she?” he asked her. His nose wrinkled. “No time to give you a bath, I’m guessing.”

“Oh, give them a break, Dean,” his mom scolded. “They’re newlyweds.”

“Eileen’s got your boy wrapped around her finger,” Bobby said. “I like her.”

“Speaking of,” Mary muttered. “Looks like Cas is being kept busy, too.”

Dean had avoided looking toward Cas, but he couldn’t avoid it any longer. When he looked over, Daphne had a pair of tongs too and was standing with Cas at the grill. She had a hand on his back. As Dean watched, the hand moved up and down, up and down. And Cas didn’t move away. _I bet she doesn’t even know how to grill a thing,_ Dean thought. He forced himself to look away, back to Willow, who was nipping at his chin playfully. He saw his mom watching him. He ignored it in favor of scratching Willow under the chin.

The day did not get any better. Charlie was her usual cheery self, but besides a few minutes she spent cracking jokes with Dean, she seemed content playing with Willow and chatting with Gilda about the episodes of _Peggy Carter_ they’d watched together _._ Dean spent most of his time commiserating with Eileen about how difficult it was to live with Sam while Sam sat and looked injured. However, while it was great to catch up after a few weeks away, it was sometimes difficult for Dean to concentrate on the conversation when he saw out of the corner of his eye how close Cas and Daphne were standing.

Cas had only spoken a few words to him. He’d asked Dean to pass the relish, then after standing around awkwardly for a few moments with an uneaten hot dog in his hand, wandered back over to where Daphne was lounging on a blanket. The blanket looked like one from Cas’s apartment, one that he occasionally draped over his bed when the weather got cold and his heat was acting up. It made Dean a little uncomfortable to see someone else other than Cas on that blanket. 

Eventually the others joined them in a tight circle on the blanket. Mary and Bobby laughed it off and said they’d stay in their chairs. “Not sure I’d be able to get back up,” Mary said with a snort. “You youngsters enjoy your joints while you can.”

Being called a youngster at 33 was hilarious to Dean, but Sam, already situated on the blanket with Willow in his lap, gave him a reproachful look for not joining them on the blanket. _Rich,_ Dean thought, _for a person who hasn’t spoken to me properly for two weeks_. But after he finished his beer - his third? fourth? - he sat partly on the blanket between Eileen and Gilda, though he angled his body outward so he wouldn’t have to look at the two inches of scant space between Daphne and Cas. 

He watched two young people toss a frisbee back and forth between themselves for a few minutes and tried to remember when it was last that he and Cas did something by themselves - just two best friends spending time together. It must have been at Sam’s wedding, or in Sam’s backyard playing with Willow. Every interaction after that had been with other people. With Daphne. He wondered if he and Cas would ever spend time together again, the way they used to. 

Eileen bumped his shoulder. He twisted around to look at her. “You okay?” she mouthed.

Dean gave her a crooked smile. “Always, gorgeous.”

He’d done a good job of tuning out the conversation the group was having, but now that he was tuned back in, he heard Daphne give a soft laugh at something Sam said, then Cas’s soft murmur. Dean couldn’t make out what Cas had said - it must have been meant for Daphne alone, then, which meant Cas had leaned in and -

Dean wanted nothing to do with that particular train of thought. Eileen had already rejoined the conversation at the commotion, but Gilda was looking at Dean with a frown. It was the first frown Dean had ever seen on her face, and her sincerity touched Dean.

“You seem distracted,” she said to him.

Her perfume was floral - but it was deep and slightly herbal, without the cloying sweetness of most, and it made Dean a little groggy. He could feel eyes on him and bitterly, without knowing why, he wished it was Cas watching him. He leaned in to Gilda. “Have a lot on my mind,” he said, and he threw in a small quirk of his mouth for good measure.

Gilda seemed unaffected. “I hope you’re enjoying the nice weather, though,” she said, responding to his smile with one of her own.

“It’s a nice distraction,” Dean said. Then he dropped his voice. “I wouldn’t mind another one, though.”

Gilda blinked a few times, like she was trying to puzzle out his meaning. 

Dean decided to help her out a little. “If you’re free after this, do you wanna grab a drink?” Once the words were out, he was struck by how much he _really didn’t want to,_ not because he didn’t like Gilda - he did; she was perfect - but because she wasn’t what he wanted. But he maintained his charming smile despite it because Gilda deserved follow-through, even if Dean couldn’t manage sincerity.

Gilda smiled at him and reached up to touch his hair gently. There was movement behind her - someone was getting up from the blanket - but Dean was too surprised by the feeling of Gilda’s hand near his ear that all he could do was gape. Then Gilda said, very kindly, so softly no one else could hear, “Sorry, but no.”

Dean’s eyebrows rose. His mouth dropped open, just a little. Then, taking her hand in his, he laughed. He couldn’t help it. 

Gilda’s smile was affectionate. “You’re not interested in me, Dean,” she said. 

Dean couldn’t stop grinning, amazed at this creature who knew him better than he did himself at the moment. “You’re something else,” he replied. 

All throughout this exchange, the rest of the group had been murmuring softly against the backdrop of barking dogs and children yelling in the distance. Dean had assumed they’d been giving him and Gilda some space, but once he’d dropped Gilda’s hand and they both looked around, he noticed two of the group missing.

“What’d I miss?” he said, mostly because one of those who’d gone missing was Cas. The other was Charlie.

Sam was frowning at him. “Charlie just got up and left suddenly. She looked upset. Cas went after her.”

“Upset?” Gilda repeated. “Why was she upset?”

Daphne was staring at Dean. Dean refused to look at her. He got up and dusted off his hands. “I’m gonna go after them.”

But Eileen grabbed one of his pants legs. When he looked down at her, she was shaking her head. “Not a good idea,” she said. The look in her eyes told Dean she knew more than she let on. “Trust me.”

Dean stared at her. Finally, he nodded. He sat back down, and those remaining descended into an uncomfortable silence.

 

Fifteen minutes later, Cas returned. His expression was grim, and he was staring straight at Dean.

“Dean, may I speak with you?”

Dean knew better than to argue when Cas was like this. He got up. Eileen grabbed his hand just for a moment and squeezed, and though Dean appreciated the gesture, it didn’t bode well for the conversation he was about to have with Cas.

Cas started to walk away from the group. Dean trailed after him. They wound along the path, dodging bikers and joggers and couples with their fingers intertwined. 

“Are you taking me to Charlie?” Dean asked, more just to break the silence than for the answer.

Cas didn’t turn around. He didn’t answer either. 

They stopped a few minutes later in a part of the park that no one else had occupied. It was probably because of the bushes and brambles that had started to overtake it. Dean looked around and scratched at a spot on his arm that had suddenly started to itch. “Dude,” he said. “We couldn’t talk 300 feet that way?” he said, jerking his head to where an elderly couple were sitting on a bench reading a newspaper together.

Cas had his hands at his sides. They were in loose fists, but at Dean’s words they clenched a little tighter. “Charlie was in tears, Dean. She left.”

Dean frowned. Charlie? Cheerful Charlie who never spoke a sad word in her life? “What? Why?”

“I don’t know,” Cas admitted. “She wouldn’t talk to me about it. But you should have seen her face, Dean. She was devastated seeing you flirting with Gilda.”

The accusation that this was somehow Dean’s fault made irritation flare up in Dean. “The hell you saying?”

Cas was breathing very slowly through his nose. Dean could hear the breaths he was taking: measured, deep. “I’m saying,” Cas said, more quietly than before, “I’m saying that I think Charlie has feelings for you.”

Dean almost burst out laughing. “What? Cas, dude, that’s the most far-fetched thing anyone has ever said to me.”

“Is it?” Cas said. “She’s admired you since the day you met. She hangs on your every word. Is it so hard to imagine that someone might feel that way for you?” 

Something about the way Cas said it made Dean look away. He still doubted Charlie’s feelings, but the fact remained that Charlie had left because he’d been flirting with Gilda. He ran a hand through his hair in frustration. “Even if that’s true - how was I supposed to know, Cas? I can’t read minds - “

“Self-awareness, Dean!” Cas interrupted. His cheeks were pink, and he pressed his lips together after his outburst. More controlled, he added, “You’ve analyzed everybody else’s lives down to the molecule when you should have been taking a look at yourself and the thoughtless way you act. The way your thoughtlessness affects other people. You decided what was best for Charlie without her knowledge, thinking you knew better, but your arrogance kept you from seeing any other possibility besides the one you deemed suitable. And you were breaking her heart the whole time.”

Dean was taken aback. His ears were hot, his eyes damp in mortification. He tried to respond, but what could he say? Dean had no defense.

Cas took in a shuddering breath. His eyes were damp too, but he didn’t tear them away from Dean’s. “Your attempts at helping your friends have been well-intentioned. You have always been kind, and I can’t fault you for that. But your actions have also been steeped in arrogance, and it’s blinded you. It’s kept you from seeing so much.” Finally he tore his eyes away to stare down at the ground. “You’ve been indulged for too long, Dean. I refuse to take part.”

All Dean could do was watch Cas walk away. Dean’s vision blurred the farther Cas got, and it was only halfway to his own car that he realized he had hot tears on his cheeks.

 

He went home. The creaky front step bothered him more than ever, but he couldn’t find it in himself to fix it. He was still reeling from Cas’s outburst. _I refuse to take part,_ Cas had said, and Dean could only conclude that he meant he refused to take part in Dean’s life. Was that it, then? What that the end of their friendship? Would Cas never hug Mary again? Would he never meet Dean’s future niece or nephew? He couldn’t wrap his head around the concept of a life without Cas, not after 16 years, couldn’t quite comprehend the possibility of it. But what else could he conclude? Cas had walked away, presumably back to Daphne, presumably forward into a new life where he moved to be with Daphne and her parents and left Dean and his family behind.

And beyond Dean’s worry about Cas was his worry for Charlie. He still didn’t quite understand where he had gone wrong. Could it be true that Charlie had feelings for Dean? It didn’t feel remotely possible, but when Dean dialed Charlie’s number, it went straight to voicemail, and it was obvious that Charlie didn’t want to speak with him. 

He sent her a few messages in a row. 

_Are you okay?_

_I’m sorry._

_Do you need anything?_

_Please call me._

At around 9:30pm, after hours of restless pacing and near-obsessive cleaning, Dean left his house. He drove to the corner store and stocked up on junk, bought a ridiculously overpriced gift bag, and left the gift bag with the junk food inside it outside of Charlie’s apartment door. He could hear movement from behind the door, so he knocked, despite knowing she wouldn’t come to the door. 

“Charlie, it’s me!” he said. “Can we talk?”

All movement from beyond the door ceased. He imagined Charlie freezing in the act of pouring herself a bowl of cereal or eating straight from the bag. He waited. No one came to the door.

He went back to his car. _Left you some things outside,_ he messaged her. _Let me know when you’re ready to talk._

She didn’t reply.

 

The next day was Sunday. After a restless night in bed, Dean needed nothing more than to get out of the house. He called his mom and let her know he’d be joining her for lunch. He was looking forward to a long conversation, alone with his mom in her dining room, but he was surprised when he parked in her driveway that there was another car parked out front as well. It was unfamiliar.

He knocked on the door, a little anxious. The door opened. Daphne stared at him with round eyes.

“Oh,” she said. “Hello. Your mom said you’d be coming by. We’ll only be a few minutes.”

Dean didn’t bother asking who “we” was. He didn’t answer her. He walked into the living room and found Cas and Mary sitting on the couch facing each other. Cas’s mouth was set in a firm line, but he met Dean’s eyes at least. Dean was the first to look away.

Mary smiled at him, oblivious to the tension. “Hey,” she said. “Sit down. Cas was just saying he was gonna go off on a writing trip.”

Dean took an armchair next to Mary and tried to find his voice. “A writing trip,” he said. 

Daphne came and sat next to Cas. Her skirt brushed against Cas’s pants leg.

Cas fidgeted a little bit, but he answered Dean steadily. “Just for a week or two. Maybe more. Don’t know where I’m headed yet. Just needed to… get away for a little bit.”

Mary put a hand on Cas’s knee. “Come back as soon as you can, okay? Dean’s been so busy lately that I’ve barely had any company. And then he left so early yesterday - oh, by the way, Dean, how’s Charlie?” She nudged Cas and grinned at Dean affectionately. “He visited her last night to see how she was doing.”

Dean hadn’t told her all the details. He’d fudged some of them on purpose, actually, but the gist had remained the same: Charlie had been upset for some reason, and Dean had gone to see her. He tried to smile, but it probably came out more like a wince. “Didn’t open the door, actually.”

Mary frowned. “That seems so unlike her. I hope she feels better soon.”

Dean didn’t answer.

Cas offered Dean a tentative smile, so small it was barely there. But his voice was kind. “That was thoughtful of you,” he said.

“The least I could do for her,” Dean replied. It was the truth. “She puts up with a lot from me.”

“Your friendship has given me a lot of comfort over the years, Dean,” Cas said slowly, looking at his coffee cup. “I imagine it’s the same with any of your friends.”

It felt like an olive branch. An apology that Cas couldn’t give with Mary and Daphne in the same room. Dean took it all the same. Maybe one day they’d be friends again. The way they had been before Charlie, before Aaron, before Daphne came back. He could only hope so.

Cas stood up. “I should be going. Daphne’s going to drop me… somewhere. I’m not sure yet. But I’ll let you know when I’m there.” He said the last bit to Mary, not to Dean. He hugged Mary. “I’ll see you soon.”

Then he turned to Dean. Dean was so grateful for Cas’s friendship he could feel it choking him. Cas squeezed his shoulder. “Take care, Dean,” he said, so low Dean could feel it in his bones. How had Dean never noticed how blue Cas’s eyes actually were?

Then Cas’s hand was gone from Dean’s shoulder, and he and Daphne were out the door.

 

Dean received a message from Charlie in the early evening on Thursday, four days after Cas left. He was already dressed for bed despite it barely being 8pm when his phone lit up and buzzed on his nightside table. 

_Are you free?_ the message read.

 _Yes,_ Dean said immediately. _Can I come over?_

 _Bring beer_ was all Charlie replied with. That was an easy enough request to comply with: since Cas had left, Dean had been steadily working his way through the nearest liquor store and had a few six-packs in the fridge already. 

Within five minutes, Dean was dressed and in his car. He didn’t know what to say to Charlie anymore; he’d drunk himself into a stupor on Sunday night and had then thrown himself into his work for the next few days, so much so that he had forgotten all of the things he’d been planning on saying to Charlie if and when she ever responded to him. All he could think to say now was “I’m sorry,” and in the grand scheme of things, that seemed to fall short of everything he needed to say.

Charlie’s apartment was a decent size for a young lady, located in a neighborhood that she shouldn’t have been able to afford - but she was good at what she did and she was paid well for it because she made sure that her bosses knew that no one could match her talents. Charlie was charming, but even more so than that, she was shrewd. Dean was so proud of her. 

He knocked on her door barely 20 minutes after she messaged him. She answered with a smile. She was wearing another T-shirt bearing another obscure reference, and her orange and green plaid pajama bottoms clashed horribly with her hair.

Once he walked in, she immediately took the beer from his hands, put it on the counter, then threw herself at his middle, squeezing until he felt himself wheeze. 

“Hello to you too,” he said, once she had let go. “I’m surprised you even agreed to see me.”

Charlie already had a beer open. She tilted her head at him. “I couldn’t stay mad at you,” she said. She walked off to her couch, clearly expecting Dean to follow. “Especially since you had no idea why.” The look she sent over her shoulder was sly. It made Dean feel a little better, if more than a little confused.

“Uh, yeah,” Dean agreed. “About that.” He took his time joining her on the couch, mostly to gather his thoughts and to send a wish up into the universe that Charlie would forgive him after what he had to say. “Cas - uh, well, he told me what he suspected. And I just wanted to say I’m sorry - I’m sorry for flirting with Gilda… but also, I’m sorry because I… I’m not interested in you.”

Charlie, who had been taking a long draft of beer - Dean had taught her how to drink - spat it all back out. It sank into the plush carpet under her coffee table, staining it. Dean pulled his legs away from the spill, but Charlie seemed unmoved. She was staring at Dean like he’d grown a third eyebrow in the middle of his forehead and it was crawling to join up with the others. She seemed both terrified and mortified. After a long pause, she finally managed to say, very mildly considering her expression, “ _What?_ ”

“Did I - Cas got it wrong, didn’t he?”

Charlie was still staring at him in horror. “Dean Winchester,” she said. “You are not seriously telling me that you didn’t know.”

Dean braced himself. “Know what?” 

Charlie hit his arm. “You idiot,” she said. She hit him again, harder this time. “I’m _gay!_ ”

Dean barely felt the pain past the difficulty he had processing her words. “You’re...gay.” He brought his hand up to his arm as an afterthought. “You’re gay?”

Charlie hit him another time, this time with a fist. “I literally told you the first time we met that Emma Watson was sexy.”

Dean put a hand over his eyes. The embarrassment was sinking in, hot and inescapable. “That’s a _fact,_ not an opinion!”

Charlie had been pulling her arm back for another hit, but she stopped. “True,” she conceded. “But come on. I wasn’t hiding it from you!”

“But you were!” Dean said. Then, “...Weren’t you?” He felt a little hysterical. “I was setting you up with Aaron and you _didn’t say anything!”_

Charlie hit him again. It really hurt this time. “You were _what?_ ” she shrieked. She sounded legitimately terrified. “ _Dean Winchester, he’s gay too!”_

“I know!” he yelled, “I heard, alright! Stop hitting me!”

Charlie’s face was bright red. She pulled her legs up onto the couch and hugged them to her chest. “I thought you were introducing me to your boyfriend,” she said a little defensively. “You never _said_ anything about setting me up.”

Dean groaned, but he didn’t answer. He was too busy pinching the bridge of his nose and trying to detangle the mess of thoughts in his head. How could he have fucked up _this much?_ Setting up a gay man and a lesbian woman together? Not seeing that the gay man had the hots for Dean himself? “I _suck_ at this shit,” he finally said out loud. He had been so confident setting out. _How had he been so confident setting out?_

Charlie put a hand on his back. “Does it make you feel better that I’m not actually attracted to you, though?”

Dean opened his eyes and looked at her. Her ears were still pink, but she was at least still talking to him. “I’m just glad I didn’t have to break your heart,” he admitted. He motioned to her, and she came to him easily, fitting into his arms with a happy sigh.

“So what is it?” Charlie said into his shoulder. “Am I not woman enough for you? Too nerdy? What?”

Dean laughed. It felt nice to laugh again. He kissed her on the forehead. “Charlie, you’re a treasure and anyone would be lucky to have you - but no. I just - I dunno. Can’t get any sparks going.” He pulled away and put a strand of hair behind her ear. “Tried with Gilda, but yeah, nothing going.”

Charlie grinned. “It’s probably because she’s into women too.”

Dean dropped his hand. The absurdity of the situation took some time to sink in. When it finally did, all he could do was collapse back onto the arm of Charlie’s couch and stare at her ceiling. “Never let me speak to another person again,” he said. 

“Yeah,” Charlie said, a bit too readily for Dean’s taste, “Probably a good idea. By the way, sorry for not responding to your messages.” She paused. “Gilda and I have been… getting to know each other.”

“Ugh.”

“That’s why I was upset at the park. You didn’t know. She didn’t really know. We had a nice, long… _conversation_ about it afterward.” She patted his knee in satisfaction. “So everything’s great.”

The indignity of Charlie getting laid while Dean definitely wasn’t, was lessened by the fact that in all honesty, she deserved it. 

He sighed. Despite being thoroughly humiliated by his piss-poor people-reading skills, Dean actually felt relieved. He’d fucked things up with Aaron, sure, and that would bother him for a while yet, but Charlie and Gilda? That had worked out, even though, Dean had to admit, it had been no thanks to him. Still, it was nice to be able to lay his head back and not worry about Charlie or Aaron or Gilda. 

“How’s Cas?” Charlie asked, effectively popping the bubble of peace that Dean had almost convinced himself was real.

Dean closed his eyes and crossed his arms over his chest. He tried to keep his voice steady and detached. “Dunno. Went on a trip. Don’t even know where he is.”

“Oh,” Charlie said. “Not far, apparently. Gilda said he’s been staying at Sam’s. He actually dropped by Gilda’s place today to talk to Daphne.”

Dean’s heart had sunk with every new word that came out of Charlie’s mouth. Cas had been staying with Sam, and Sam hadn’t said a word? And Cas was still visiting Daphne? One of the few ideas that had comforted Dean about this trip of Cas’s was that he was supposed to be _away._ Yes, away from Dean, but that meant away from _Daphne,_ too. And Dean was learning it wasn’t true. Cas had gone away just to get away from Dean. 

“Wow” was all Dean said. “I guess I really did scare him away, didn’t I?”

Charlie’s voice was quiet. “I heard you guys fought about me.”

Dean opened his eyes and sent her a fierce look. “My shitty friendship skills are not your fault, Charlie.”

She shrugged. “I was dramatic,” she said. “I’m sorry. I didn’t mean - “

Dean straightened up and put a hand on her shoulder. “I mean it, lady. Stop. Cas and I fought, and yeah, it started because you were upset - but… really, it would have happened eventually. I would have done something else stupid, and he would have...he would have had enough.”

Charlie’s eyes were a little damp. “Is that why he left?”

“Guess so,” Dean said. “He said he needed to get away for a little bit.”

“Get away from you?” 

“That’s not quite what he said, but… I think so.”

Charlie’s lip wobbled. 

Terrified, Dean cast about for another reason. “I mean,” he said quickly, “you said he’s been visiting Daphne, right? They could be… giving it another shot?” Even saying it was painful.

Charlie gave a small shrug. “Gilda’s been saying that Daphne’s parents might be convinced to move back here. It might actually work out.”

“Oh.” Dean should have been comforted by this fact. Dean should have had all of his fears about Daphne breaking Cas’s heart allayed. Dean should have felt like laughing, maybe calling Cas to congratulate him. 

Dean felt none of those things. He felt, instead, a sense of horrible hopelessness descending on him, and he suddenly understood one thing very clearly: he’d been arguing against Daphne’s presence in Cas’s life as if he were afraid she might leave him again when, in reality, all he _wanted_ was for her to leave him again. He’d been acting so stonily toward her not in expectation of her leaving, but to _encourage_ her leaving.

But why? Why was Dean so against Cas having this woman in his life? She cared for Cas. She hadn’t meant to leave him the first time. In fact, she had, up until leaving, been a great companion for Cas. So why couldn’t Dean accept her? If it was a real possibility that she could stay this time and provide for Cas in ways that Dean couldn’t - why did Dean want to stand in her way so badly?

As he asked himself these questions, the answer to all of them settled softly in Dean’s consciousness, as softly as the hand that Daphne stroked over Cas’s back, as softly as the skirt that Daphne let sweep over Mary’s couch. He put a hand over his eyes and laughed.

Charlie, who had been watching Dean’s expression very closely, spoke up tentatively. “Dean?”

Dean shook his head. The laughter was very quickly turning into something else entirely - something more wild, something more bitter, something more sad. “Charlie, I - I think -”

Charlie’s devastated face told him she already knew. “Oh, my poor bisexual boy,” she crooned. “I am so sorry.”

 

Charlie made him sleep on her couch. He was too overwhelmed to drive home, she had told him, and when he still tried to sneak out, she’d caught him and threatened to call Cas. That had been an effective deterrent, so Dean had borrowed a toothbrush and settled on her couch in his jeans. 

Lying there, his mind raced. Despite the dark and the steady hum of Charlie’s fridge, he couldn’t stop thinking. Charlie had been right - he was overwhelmed. Overwhelmed with the things that he should have known, one of those particular things being the knowledge that all of his friends were apparently _gay,_ and that he’d been applying an embarrassingly heteronormative worldview to them despite his being quite comfortably bisexual himself. It was embarrassing and jarring and sad and pitiful, and it underscored just how poor he was at the thing he’d believed himself to be so good at: _people. Life. Success._ Dean’s previously perfect life didn’t seem so perfect anymore, not when Dean could count, off the top of his head, _at least_ three people he’d misjudged, three people whose lives could have been forever changed for the worse if their own smarts hadn’t saved them. 

And those three people didn’t even include Dean himself, the person who, arguably, Dean had misjudged the most. It was, after all, his lack of self-awareness that had started this whole situation. It had led him into the dangerous quagmire of making himself to be Charlie’s mentor when, in fact, she had not needed one, and when, in fact, he was probably the last person she would have needed if she had. That, in turn, had led Dean into calling Aaron and then eventually disappointing somebody who had only ever tried to be what Dean wanted.

But what was really plaguing Dean’s consciousness and keeping him from sleep was the fact that his lack of self-awareness had kept him from realizing the _real_ thing that he wanted.

That thing was a person.

And that person was Cas.

Dean wanted Cas, and it was a wanting that had dug itself so deep into his subconsciousness it had become a part of him: an ache that had developed so slowly over the years that even as it worsened, he was learning how to nurse it so that he could pretend it didn’t exist. He was sure that occasionally he’d felt it over the years - in the cold, mostly, acting up when he was at his lowest - but for the most part he’d been able to tuck it away.

Here, however, lying on Charlie’s couch, trying and failing to recuperate from the barrage of revelations he’d suffered, the ache he felt for Cas was overwhelming. He wanted Cas in his house, in his bed, in his arms - he wanted Cas’s breath in his lungs and Cas’s hands in his hair. He wanted Cas. 

And Cas was currently an hour away, only three houses down from his ex-girlfriend.

And despite Cas only being a few dozen miles away, distance was not what Dean meant when he thought, _He’s too far. And I’m too late._

Self-awareness was a bitch.

 

Three weeks later, Dean parked in front of Mary’s place and stamped out the disappointment he felt at not seeing Cas’s car. Dean had not heard from his best friend since Cas had left town, but he’d harbored hopes that maybe Cas would show up and surprise Dean. Because Dean was ready to see Cas. He had been ready to see Cas for a few days.

Dean had already come to terms with his feelings for his best friend. That had been the easy part. The next part - accepting that Cas might very well come back hand-in-hand with Daphne - had been heart-wrenching. It had taken quite a few beers to even begin wrapping his head around it, and even more to admit that Cas’s happiness was more important to him than his own. But he’d done it. And he was ready to see his best friend and accept whatever choice Cas had made. But Cas, apparently, was not ready to see Dean.

Dean hitched on a smile when the door opened, only to see Sam behind it, already giving him the puppy dog eyes. 

Dean scowled. It wasn’t a nice emotion, irritation, but it was at least better than the sadness Dean had wallowed in immediately following his epiphany. “Finally answering _something_ , huh?” Sam had been dodging Dean’s calls, presumably to hide Cas’s presence. It was only through Eileen that Dean even knew his brother was alive. “I already knew you were hosting Cas, so you were being an avoidant dick for no reason.”

Sam winced. “Dean - “

“Save it,” Dean muttered, shoving through the door. “I’m not gonna force mom to deal with my bad mood, so don’t put me in one.”

Sam sighed heavily, but he shut up. He followed Dean into the kitchen. Right before Dean opened the back door, however, Sam made a tentative noise. “Before you open that door - “ he started, but Dean was already holding up a hand.

“Nope. Not ready to talk to you.” He opened the door.

The occupants of the backyard turned to look. Charlie was there, playing with Willow. Gilda was in a shawl and smiling at Charlie. Bobby was halfway through a burger, and Mary - Mary was turned toward Cas.

Dean faltered on the back step at the sight of Cas’s blue eyes watching him. His heart felt like it stopped for a moment or two, but then it picked up its pace five times faster.

“Told you,” Sam muttered behind him.

“Not helping,” Dean said, then bit his tongue when he noticed Cas breaking away from Mary to approach him.

Sam edged out past him and slunk away toward Eileen, who was sneaking pictures of Gilda and Charlie.

Dean didn’t move from his step on the backstep of the house, not because he didn’t want to greet Cas, but because he was scared his knees might buckle if he tried. He watched Cas approach instead, knowing his cheeks were heating at the way Cas’s mouth twitched downward when he looked at Dean.

Cas’s sigh greeted Dean. It was long and heavy and regretful. “Hello, Dean,” he said quietly. He was beautiful.

Dean could hardly think. The first thing out of his mouth was almost frantic: “I didn’t see your car.”

Cas paused. Dean wanted to recoil. What if Cas said Daphne had dropped him? Where was Daphne? And why didn’t Dean already have a drink in his hand? “I rode with your brother,” Cas said. “I left my car at my apartment.”

Dean’s relief was short-lived, because none of what Cas said solved the Daphne problem. But Dean couldn’t say her name, so he nodded instead, then looked away. He met Charlie’s eye. She gave him a sympathetic smile. He wasn’t able to even think about how to respond to the sadness in her face before Cas had his hand on Dean’s arm.

“But I - I don’t have a ride home. I was hoping that you might...?”

“Of course,” Dean blurted out. “Yeah.”

Cas’s smile was sad, so sad. “Thank you,” he said. He looked down at his shoes. Brown. Sensible. Just like Daphne’s. “I missed you.” Cas’s voice was quiet.

Dean wanted to say _I missed you too,_ but it sounded hollow. There was no way Cas had missed Dean as much as Dean had missed Cas. “Not as much as I missed you, dude.”

Cas’s smile turned a little dry, though Dean got the feeling that it was more for show than borne of actual irritation. “It’s not a competition, Dean.”

“Well, if it was, I’d win.”

And Dean’s intuition was right, because Cas’s smile was back, and it actually reached his eyes. “Fine,” he agreed. “Whatever you say.”

“Mr. PhD agreeing with little old me?”

“You are, as always, smarter than you give yourself credit for.”

 _As always._ Dean had never heard sweeter words. _As always_ meant a past, and regardless of the stupid shit Dean pulled over the years, it was a past that no one could erase, not even Daphne. 

Dean patted Cas on the cheek once, just once before pulling away, and was rewarded with a surprised grin. Then Cas was doing the same to Dean, except it was less of a pat and more of a slap, and Dean was yelping in pain. 

“You jackass,” he breathed.

“A jackass you missed terribly,” Cas taunted, dancing out of Dean’s reach.

And fuck, it was true.

 

“Would you like to come up?” Cas’s voice was tentative. Hopeful.

They were idling in the Impala outside of Cas’s apartment building. They had spent the whole evening sitting together in Mary’s backyard while they listened to Sam and Eileen recount their adventures as parents of a young rescue puppy, and Cas had smiled and nodded along, adding smartass comments where appropriate and murmuring inside jokes to Dean where it wasn’t. It had been like he’d never left, and if it were left to Dean he would have preferred to pretend it was just so, for as long as possible.

Pretending nothing had changed, however, was impossible when Cas was looking at Dean like he was expecting Dean to refuse his invitation.

“If you’re inviting me up, then yeah, dude,” Dean said, laughing a little nervously.

Cas unbuckled his seat belt. “Consider it an invitation, then,” he said, and he sounded almost like himself. 

Cas’s apartment was small, but it was more than enough for a single man who only seemed to subsist either on pork rinds or kale and never anything in between. A small bedroom off to the side was nothing more than a convenient place for Cas to collapse in exhaustion; the dining room was where Cas spent most of his time, which was obvious by the stacks of notes that were scattered where placemats should have been. The rest of the apartment was clean - or at least untouched - because Cas spent 80% of the time he wasn’t entertaining Dean, writing.

Cas was tinkering around in the kitchen. “Coffee?” he asked.

Dean took a moment before he answered, jarred by the strangeness of Cas’s offer. Cas had never asked before - he’d expected Dean to make his own. “Uh, yeah,” Dean said. “Thanks.” He was being treated like a guest, and it only hurt because once upon a time, he’d been treated like family.

A few minutes later Cas brought the coffee to Dean. Dean had been looking through Cas’s notes. 

“You’ve gotten a lot done,” he said. Diagrams and sketches of settings littered the table.

Cas moved near him. His arm brushed Dean’s as he started straightening the papers. “The three weeks away were productive,” he said.

Dean took a swallow of coffee. It scalded his throat, but he managed to ask, “Yeah? Why’d you come back then?” _If Daphne was such a source of inspiration, why are you here?_

“I have a home here,” Cas said. He wasn’t looking Dean in the eye. He kept rearranging the stacks of paper. “I missed it.”

Dean nodded. He picked up a paper that Cas dropped and admired the sketch on it. Cas had always been a decent artist, though he never admitted it. “Damn,” Dean said in admiration. The character on the paper was dark-haired with freckles scattered across his nose. He was sitting on a hill with his head tilted up to the sun. “Who’s this babe?”

Cas moved closer. “Ah,” he said, smiling a little. “When I say I was productive these past few weeks, I mean I neglected the novel my editor’s expecting and started on a new one.”

“Yeah?” Dean asked. “That doesn’t sound practical.”

Cas took the drawing from Dean’s fingers. “Inspiration isn’t practical,” he said gently. “I’ll tell you about the story one day.” He tucked the drawing away and picked up his mug. He leaned his hip on the table and looked at Dean. He seemed to be _trying_ to be casual, but not quite achieving it.

“What?” Dean asked suspiciously.

Cas shrugged. “I also came back because - because I heard about Charlie and Gilda.”

“Oh.” Dean blinked. “Okay.”

Cas’s eyes were shifting between Dean’s, trying to find something that Dean wasn’t quite sure existed. 

“What?” Dean asked, a little startled. “What does that have to do with me?”

Cas frowned. He had his mug in his hands but he hadn’t taken a sip of it. “You - you and Gilda. You must have been disappointed.”

Dean took a moment to let that sink in. Then he laughed. “Cas,” he said, putting his mug down and putting his hand on Cas’s shoulder. “ _Cas._ Oh, my God.”

Cas was squinting at him. “I take it you are _not_ disappointed.”

“ _No,_ ” Dean emphasized. He laughed some more. “Gilda shot me down real quick. Said she knew I wasn’t really interested in her. It was true, too, so I didn’t argue.”

Cas’s cheeks were pink. He looked down at his shoes. “Oh,” he said, and somehow in that one syllable he carried a dozen different meanings.

Dean dropped his hand. Punched Cas on the shoulder instead, ignoring his indignant splutter when his coffee sloshed over the rim. “You sap,” Dean said. “You came back because you were worried about me.” Dean played it off as no big deal, but he was touched. More than touched, though, he felt loved. Cas had left because of Dean, sure, but he’d also come back because of Dean, and Daphne had never managed either. 

Cas sent him a dry look through his eyelashes. “You give me many reasons to worry, Dean; it’s not a good thing.”

“Sorry,” Dean said, absolutely not sorry. “You’re gonna worry about me until one of us dies.”

Cas’s smile was amused and affectionate, one that he tried to hide in his mug. Dean let himself bask in the warmth. 

A few moments later, though, a minute furrow appeared between Cas’s brow, one that grew until it was apparent that whatever he was thinking was going to cause Dean no small amount of pain. Cas licked his lips, nervous, then let out what Dean assumed to be a steadying sigh.

“Don’t do that,” Dean said immediately. “Stop sighing. It’s never - it’s never a good thing when you do that.”

“I’m sorry,” Cas said, sounding sincerely, profoundly sorry. He put his mug down and dragged his hands down his face. “I just - I can’t pretend like nothing’s changed, Dean.”

Dean’s stomach sank. “What’s changed?” 

Cas hadn’t removed his hands from his face; his reply was muffled. “I don’t know how you’re going to react.”

Panic was sweeping over Dean, taking over his voice: “Then don’t tell me,” he said quickly. “Let’s - let’s pretend that nothing’s changed. If you say it, then that’s it. That’s - that’s it. It’s out, and there’s no going back.” 

Dean knew that delaying the news of Cas and Daphne didn’t mean delaying it forever; one day, he’d be forced to acknowledge their relationship, and that might very well turn out be the day of their wedding. He knew he was being irrational by making this request of Cas, knew it would make no difference in the end when Cas was with Daphne and Dean was alone. But still, he found himself wishing, hoping - _don’t tell me, not now, not now._

He had thought he could accept Cas and Daphne, but now, seconds away from the words spilling into reality, he knew he couldn’t. And then Cas would know. Cas would know by Dean’s reaction that Dean was in love with him.

In love. Because Dean _was_ in love. He loved Cas more than he knew what to do with, more than he could bear. 

Cas had lifted his head from his hands. His expression was that of one who had known he’d be disappointed but was still devastated regardless. His mouth opened and closed several times before he finally croaked, “I see.” He looked down at their mugs. “Well,” he said, after a long pause, “Let me get us some refills then.” 

He took Dean’s mug along with his own - though they were both nearly full - and Dean watched helplessly as Cas carried them to the carafe. Cas’s mouth was set as he refilled his mug, then Dean’s, but then Dean saw his best friend’s throat bob dangerously, and he knew he couldn’t take it. He’d hurt Cas once, then once again, so much so that Cas had _left -_ and now here Dean was doing it again, like Cas was nothing more than a punching bag to turn into tatters. 

_No more,_ Dean swore, and though he knew his heart was bound to ache for as long as he lived, the decision settled in his soul as _right_. Love, Dean suddenly understood, was to let Cas be in love with someone else. It meant to potentially stand next to Cas as his best man and watch him marry someone else and do it with joy because Cas was _happy._ It meant to hear Cas out when he needed to lighten his load, and to hope that the relief Cas would find in telling his secret would bind Dean’s heart tightly enough it would stop bleeding before Cas noticed.

Dean shook his head at himself. He looked at Cas, pouring creamer into his coffee. Dean steadied his heart on that image because it reminded him of what he stood to lose. Then he took a deep breath and tried not to let his voice shake when he said, “I’m sorry.”

Cas shook his head without looking at Dean. “It’s fine.”

“No, it isn’t,” Dean said, so vehemently Cas sloshed cream over the rim of his mug and looked at Dean, startled. Dean put a hand up to steady Cas’s nerves and walked to him. He took the creamer from Cas’s hand and put it to the side. “Look, Cas. What I said just now? Dumb. I’m your best friend, dude. Maybe not the _best_ best friend, considering all the shit I’ve pulled, but I know enough about friendship to know that I should have your back.” He tried to smile, took a breath, then powered through: “Whatever you wanna tell me, I’m all ears.”

Cas’s eyes were damp. But they were sincere and wide, and so, so blue, and they stared straight into Dean’s soul for long moments. When he finally spoke, his voice was low. “Dean,” he said, “you’ve always been dear to me.” 

Dean set his expression, grit his teeth together so hard he knew he’d hear it from his dentist. He nodded. He waited for the _however._

It never came.

Cas stepped in a little closer. “Dearer than I think you know.” 

The breath left Dean’s lungs when the implication began to sink in. Dean’s mouth went slack as he sucked in a startled breath. “Sorry?”

“I’m _sorry_ if this changes things,” Cas said quickly, almost laced with desperation. His eyes were almost overflowing. “But I needed to tell you; I just couldn’t take it another second, Dean. I’m sorry.”

He kept apologizing. _Why was he apologizing?_ If Cas was saying what Dean thought he was saying, apologies were unnecessary. Dean tried to say this, but the words caught in his throat, blocked by the lump that had formed. He did what he could: he reached up, grasped Cas’s upper arm and squeezed. Dean’s grip was so tight he was sure he was leaving marks, but Cas needed to know that he wasn’t alone in this.

Cas looked stunned at Dean’s reaction. He swallowed hard, but his next words were more confident, buoyed by Dean’s touch. “Dean, I know - I _know_ I’m not perfect, and I know I lecture you more than I should and I’m always irritable, but - “ He sighed, and God, this time it was the most beautiful sound in the world. “I need to know,” he continued, voice beseeching, eyes wide, “do I really not have a chance?”

As Cas spoke, a tremble took root in Dean’s fingers, in Dean’s bones. He touched Cas’s face where two tears had overflowed and blessed his skin, and felt his own vision blur through moisture.

Cas let his words sink in for a few moments, but he kept speaking when Dean didn’t begin, his eyes dancing between Dean’s, dislodging another tear. “I don’t have the words, Dean. It’s - it’s my _job_ to have words, but I don’t have them this time, not to tell you how much I love you.” He paused. Licked his lips where the tear had touched the seam. “Because I do. I love you. I love you more than I love anything else, Dean. I would give up everything for you. Everything - heaven, earth, everything in between.”

Dean shook his head and sniffed, laughed through the tears when Cas’s mouth opened again to speak. “Stop,” Dean said. “You’re repeating yourself.”

Cas laughed too. Delirious. 

Dean couldn’t stop smiling, and now his hands were around Cas’s jaw, his thumbs on Cas’s cheeks. “You’re crying.”

“No, I’m not,” Cas said stubbornly, though his nose was red and Dean’s thumbs were diverting his tears. “And even if I were, look who’s talking.”

Dean didn’t even deny it. He nodded and didn’t bother to stifle the tremble of his smile. “I thought you were going to tell me you were back together with Daphne.”

“I couldn’t do it,” Cas whispered. “I meant to. That’s why I left - to try to get over you and move on with Daphne. But I couldn’t do it.”

“We’re a couple of fucking clowns,” Dean whispered.

“‘ _We,’_ ” Cas repeated, licking his lips nervously. “Does that mean that you - I don’t want to assume - “

Dean had his hand cradling Cas’s face, and Cas still had to ask. Dean skated a thumb over Cas’s bottom lip. “Yeah, genius.”

Red bloomed high on Cas’s cheeks. “I love you,” he said again, seemingly out of nowhere. He sniffed, then laughed a little at himself. “Sorry.”

Dean searched Cas’s eyes. “I dunno how to - is it okay - “ He closed his eyes and took a deep breath before trying again. “Cas, can I kiss you?”

Cas’s mouth went slack. His lips were swollen already from the tears. “Yeah,” he breathed.

Dean hadn’t let himself imagine what it would be like to kiss Cas, had decided almost as soon as he realized he had feelings for Cas that there was no future for them anyhow, so he’d locked up whatever thoughts he may have once had about Cas’s lips and shoved them into the attic of his brain. Because of this, the hesitation he showed before kissing Cas was genuine. He’d kissed a lot of people, but this was Cas, the person he’d called family since he was 17 years old and angry at the world, and no kiss could ever communicate the depth of gratitude Dean had for him.

Cas licked his lips. “You don’t have to,” he said softly, “if you don’t - if you’re not sure.”

The absurdity of that statement and the hurt in Cas’s voice spurred Dean on. He leaned in and kissed his best friend, just once. It was nothing more than a slight shift of lips against Cas’s, but it was more than enough to steal Dean’s breath away. When he drew back, Cas kept his gaze trained on Dean’s, watching for a reaction.

Dean ran a thumb over Cas’s bottom lip, drawn to the warmth of the breath leaving Cas’s lungs. “I have never been more sure of anything else, Cas.” Then he swallowed and said, “I love you too, you know.” He’d never said it to anyone before, had never felt the inclination, but he knew the truth of it. “I’m sure of that too.”

Cas’s cheeks bloomed red. The hands he had on Dean’s waist clutched a little harder. “Why didn’t you ever - ?”

“I didn’t realize,” Dean whispered, daring to lean in again, loving the way he could feel the rise of Cas’s chest against his own. “But I hated seeing you with Daphne, and I couldn’t figure out why.”

Cas was the one to lean in the rest of the way, an apology written in the furrow between his brows. His lips were warm, flushed from the tears, and Dean wanted to sink into the gentle way Cas handled him. 

Truthfully, it was a little surreal to be kissing his best friend after 16 years of decidedly _not_ kissing, but Dean, hearing the soft noise of pleasure at the back of Cas’s throat, was eager to get to a point where it was commonplace. Daily. Hourly. Honestly, if they never ever stopped, Dean wouldn’t complain. 

When they parted, Cas looked overwhelmed: his blue eyes were dark, his lips were still parted, and the grip he had on Dean’s waist was tight enough to leave marks.

“We’re doing that again,” Dean murmured, thrilling in the way Cas licked his lips.

“Does that mean this is the end of Dean Winchester, the lifelong bachelor?” Cas said, a dry smile making Dean’s knees weak.

“I’m never hearing the end of that, am I?” Dean said. His happiness was something alive, vibrating so hard under his skin he was sure Cas felt it through the hands around his face.

“I can’t say it if my mouth is otherwise occupied,” Cas said, grinning wickedly.

Dean stared. Took a breath. “I think I can work with that,” he said numbly.

 

Lying in bed with Cas, the love of his life, was a little different from lying in bed with Cas, his best friend. There was much more touching, for one, and most of it was intentional. There was also the knowledge that this time was just the first of what could potentially be a lifetime’s worth of bed-sharing, an idea that Dean swore he’d work his hardest to make possible, though he wasn’t quite sure how to voice that promise. In the meantime, he was reveling in the novelty of the warmth of Cas’s leg slung over his own.

“I’m sorry I left,” Cas whispered after almost an hour lying silent, forehead pressed to Dean’s.

They were so close it took next to nothing for Dean to arch in and kiss him. He hoped Cas would stay this close forever. “I’m sorry I made you.”

Cas touched his thumb to Dean’s bottom lip and dragged it down, a habit that he’d already formed in the short time they’d been together. “I was scared of who I thought you were becoming. Thoughtless. Selfish. I thought I’d encouraged you to be that way.”

Dean’s ears burned in mortification. He took Cas’s hand and held on. “I was an asshole,” he said. He kissed Cas’s knuckles. “But it wasn’t your fault. You’re the only one who keeps me in line.”

“You were thoughtless,” Cas corrected, “but you weren’t an asshole. I only tried to make myself believe that you were because it would have been easier to leave.”

“Eager to ditch your best friend, huh?” Dean asked, trying not to sound wounded. Judging by Cas’s frown, he’d failed.

“I was convinced by then that I’d never be with you,” Cas explained. “You were flirting with Gilda, and you’d… never shown me any interest.”

Dean’s mouth twitched upward. “Oh, so when you called me out about the flirting, it was because you were jealous?”

Cas rolled his eyes, but his cheeks were pink. “I really did believe you were breaking Charlie’s heart, and I was astounded that you hadn’t realized - but… yes, I also left because I couldn’t stand not being with you.”

Dean gave Cas the softest of smiles. “I’m glad you changed your mind,” he said.

“I didn’t,” Cas said. He laid his palm on Dean’s chest and let the warmth of his skin sink into Dean’s. “I still wouldn’t be able to stand not being with you.”

“Good thing I agree,” Dean said, curving his hand around Cas’s cheek and blushing when Cas turned his face to kiss his palm, watching Dean’s face the whole time. Dean’s throat went dry; he licked his lips. He was disappointed when Cas closed his eyes and stifled a yawn.

“Do you think your family will be surprised?”

Dean had barely spared a thought for anything else besides Cas for the past few hours. He blinked. “Oh.”

“...You were planning on telling them, weren’t you?” Though Cas’s eyes were closed, his voice was soft, a little scared.

Dean remembered the way Cas’s voice had faltered earlier before Dean had kissed him. He made another promise to himself: to never let Cas go one second in doubt of Dean’s feelings. He smiled and hid his face in Cas’s neck. Cas smelled like salt - sweat, tears - and his citrus shampoo. “We can tell them together,” he said against Cas’s collarbone. 

Dean heard Cas’s throat click as he swallowed. “Really?”

“Tomorrow.”

“ _Tomorrow?”_

“Why wait? It’s a Sunday; they’ll all be home.”

“We’re going to tell them in person?”

Dean landed a kiss on Cas’s neck before pulling away. “Why not? Making Sammy cry has always been fun.”

Cas searched Dean’s eyes as if he were trying to find any evidence that he might be lying. He would find nothing, Dean knew. Cas’s smile was slow to spread, but spread it did until all Dean could see of Cas’s eyes were shining blue half-moons.

“Okay,” Cas said. 

“Okay,” Dean replied. Simple. Easy. 

 

Mary opened the door before Dean even lifted his hand to knock. “Saw you from the front window,” she explained, then let them in.

“You look out the window a lot?” Dean asked, sitting down on the couch he’d known since he was 17. Cas settled down next to him, though he left a decent amount of distance between them. Dean patted his shoulder in gratitude; though he thought Mary would be ecstatic for them, he had no real idea how Mary would react.

“When I’m bored,” Mary admitted. “Which is a lot.” She sent Dean a pointed look. “Planning Sam’s wedding was the highlight of my year, you know.”

Dean’s ears burned at the hint. “Seriously, mom?”

Mary shrugged and leaned back in the armchair. “Can’t blame a mom for wishing,” she sighed. Then she looked at Dean, then at Cas. “So. What trouble have you guys gotten in that you don’t even call ahead?”

Dean and Cas looked at each other. 

Mary looked between them. “What is it?” she asked, starting to get a little frantic. “Sam? Eileen? Bobby?” Her hands rose and fell, unsure what to do. She pressed one to her lips.

Cas reached forward and took the other hand, trembling on her lap. “Mary,” he said gravely. He took a deep breath.

Mary’s eyes watered.

“Cas and I are together!” Dean blurted out.

Cas looked at him, affronted.

“You were scaring her to death, you idiot,” Dean hissed.

“I was _not_ scaring her to death.”

Mary sobbed.

“For fuck’s sake, Cas,” Dean muttered, moving toward her. He crouched in front of her and put a hand on her knee. “Hey. Sorry. He’s - he’s miserable at this.”

Cas scowled.

“But we’re also dating,” Dean added. “Since last night.”

Cas rolled his eyes.

Mary tried to catch her breath. Her smile was wobbly. “I knew it would happen,” she said shakily. She reached for Dean, and Dean, relieved, let her fall forward and embrace him. “I’m so happy for you,” she said, sniffling.

Blindly, Dean reached out a hand in Cas’s direction, smiling when Cas took it. 

“Also,” Dean said, as casually as he could manage, “I’m probably going to ask him to marry me within the year.”

 

“What makes you think I’d say yes, anyway?” Cas said, as they walked up Sam’s driveway. Cas had been angry with Dean throughout the car ride, mostly for making him cry again. 

Dean nudged him with an elbow, grinning when he saw a hint of a smile at the corner of Cas’s mouth. “Oh, I dunno,” he said. “What was it you said last night? You’d give up everything for me? You don’t have the words to tell me how much you love me?”

Cas’s cheeks were aflame, but he was biting back a smile. “You’re incorrigible.”

“I love it when you speak nerdy.”

Cas shook his head, but the smile burst through anyway. He quickened his pace and knocked on Sam’s door before Dean could rub it in. By the time Dean caught up to him, Sam was opening the door, Eileen poking her head under his arm in curiosity.

“You’re not neighbors.”

“Nah, just us,” Dean said, slinging an arm over Cas’s shoulder. “Your friendly neighborhood Dean and Cas.”

Eileen rolled her eyes. “I guess you can come in,” she said, sighing heavily. Then she smiled. “If I get a hug.”

Cas gave her a hug first, then Dean. He kissed her on the forehead for good measure.

“We were planning on going out for lunch,” Sam called over his shoulder. He was walking to the kitchen. “You’re welcome to join us.”

“We have plans,” Cas said, though Dean hadn’t been aware of any. “We just wanted to stop by and tell you guys something.”

When they rounded the corner, they found Sam measuring out dog food into a bowl. Eileen joined him to pick up Willow where the puppy had been sitting patiently.

“Sounds suspicious,” Sam said. He dug his measuring cup into more dog food.

Dean took a deep breath.

“Dean and I are together,” Cas said, smiling cheekily at Dean. His expression turned startled when he heard the clatter of the dog food container on the floor.

“You okay, Sammy?” Dean asked, as Sam cursed quietly and bent down to clean up.

Eileen didn’t bother to help. She put Willow down. “Say again?” she said, looking confused. Her hands came up to sign along with her words like it did when she was flustered. 

“Dean and I are together,” Cas repeated.

She shook her head, disbelieving. “I don’t understand.”

Dean took Cas’s hand and held it up for her to see. “We’re together.”

 _That_ made Eileen put a hand over her mouth. “Oh,” she said, her eyes suddenly very round. Her lips trembled a little when she smiled, but Dean had very little time to contemplate it before she was throwing herself at Dean. “Big brother,” she said from somewhere around his chest, “You made a good choice.”

Dean looked at Cas over Eileen’s head. She couldn’t hear him, but what he said next was for Cas anyway: “I did, didn’t I?”

Eileen released Dean, patting his cheek affectionately. Then she turned to Cas, visibly moved. “My other big brother,” she greeted, before pressing her face into his collar. “Hello.”

“Hello, little sister,” Cas said into Eileen’s hair, and that was mostly for Dean.

When Eileen drew back, she smiled at both of them. “Sam, do that later,” she said, turning to her husband.

“Yeah,” Sam croaked. He was still crouched down, facing away from them. 

“Shit, Sammy,” Dean said weakly. “Are you crying?”

Sam didn’t answer. His shoulders started shaking. Dean looked at Cas, helpless. Eileen just looked gleeful. 

_He didn’t even cry at our wedding_ , she signed. Then she frowned suddenly. _Asshole._

Sam straightened. His nose was red, but his eyes were dry. His cuffs, however, were suspiciously damp, and none of the spilled dog food seemed to have moved. He cleared his throat. “I guess congratulations are in order, then,” he said. His smile was wobbly. He moved toward Cas first and engulfed him in a huge embrace. “I had almost lost hope for you two,” he said, and by the time he turned to Dean, he was openly weeping.

“There’s a lot of goddamn crying for what’s supposed to be good news,” Dean grumbled into Sam’s shoulder.

Eileen was leaning against the counter. She had a hand on her stomach. “Sam and I are having a baby, by the way.”

 

They stayed for most of the day, calling Mary and Bobby over to tell them the good news about Sam and Eileen. Dean embarrassed himself by crying even more than his mom, but Cas’s hand stayed locked in his for most of the afternoon, which made up for it. 

Bobby was the only one who didn’t shed a tear at Dean and Cas’s news. He called both of them idjits for waiting so long and shook Cas’s hand, but besides that, he had nothing else to say, though Dean caught him looking their way more than once with shiny eyes, so he supposed it was something.

Later, after lunch and dinner and more than a few drinks in between, Dean and Cas made their way to Dean’s home. The conversation trailed off the closer they got to Dean’s neighborhood, and by the time they were two streets down, Dean could practically feel the anxiety buzzing off of Cas in the front seat. When he pulled into the garage and shut off the engine, the silence was awkward. Despite having basically proposed to Cas already, neither knew how to repave the road they’d already walked as best friends.

“Are you staying over?” Dean said quietly, staring straight ahead at the garage wall.

The silence was so complete he heard Cas swallow nervously. “I would like to.”

“Great,” Dean said quickly, too loudly in the quiet air. “I’ll order a pizza and we can stay up and watch a movie or something.”

He clambered out of the car before Cas could reply. He only knew Cas followed when he heard the passenger door shut behind him.

“Or,” Cas said, just loud enough for Dean to hear, “We could go to bed.”

Dean dropped his keys. “Uh, yeah,” he said, as he scooped them up from the floor. It was barely 8, but _god,_ did bed sound good. “Yeah, whatever you want.”

They went into the house and started getting ready for bed. Dean handed Cas a toothbrush still in its packaging, and later, when Cas had finished brushing his teeth, Dean stood and stared helplessly at the toothbrush leaning against his in the little mug by the tap, wondering if he’d ever get used to the sight.

When he wandered, dreamlike, back into his bedroom, he found Cas in one of his T-shirts, sitting up against the headboard, staring at his lap. Waiting for Dean.

“Hi,” Cas said.

Dean wanted to cover every inch of Cas’s body with his. He swallowed. “Hey.”

“Are you tired?”

“Not really,” Dean said, still at the door. 

“Will you join me?”

Wordlessly, Dean walked to the bed and climbed in, leaning his back against the pillow braced against the headboard and staring at the space between his knee and Cas’s.

“I wanted to talk to you,” Cas said softly.

Dean took a deep breath. “If it’s about sex, Cas, I - I don’t care. It’s not a big deal.” The night before, Dean had thought about it - had weighed the possibility of never having sex again against the possibility of not being with Cas - and it didn’t take long to decide which Dean couldn’t live without. “I’ll keep my hands to myself.”

A long, tense silence followed. “What if - what if I don’t want you to?”

Dean’s fingers began to itch. “Say that again?”

Cas was fidgeting with the comforter. “Dean, you make me… restless. I’ve never felt this way with anybody before. Even before I understood my feelings for you, there’s always been this urge to… to touch you. On your shoulder or your arm. But lately... other... places.”

The concept of _other places_ made Dean’s throat go dry. “Oh.”

“But I can’t be sure,” Cas continued, staring at his hands, palms up on his lap. “And I just wanted you to know.” He sounded so lost, so desperately lost, but Dean was no better off.

“We could...try,” Dean said lamely. He extended a hand.

Cas stared at the offering. He didn’t take it. “I don’t want to disappoint you if it doesn’t work out,” he said.

Dean snorted. Took Cas’s hand himself and pressed it to his mouth. “I’m the disappointment between the two of us,” he said. “Or have you missed out on the last few months?”

Cas’s mouth twitched upward. “And yet throughout it all I could still barely keep my hands to myself.”

“Why’re you holding back now, then?” Dean murmured, sounding more confident than he felt. 

Cas’s smile was crooked as he slowly leaned in, spread a hand on Dean’s shoulder, and dragged it down his chest. Then he twisted his fingers in the cloth of Dean’s T-shirt, right at the edge, his knuckles bumping against the hem of Dean’s boxers. 

“Should I keep going?” Cas asked. Dean watched, mesmerized, as Cas’s throat bobbed.

His fists tightened at his sides. “Only if you want to,” he said.

Cas stared at the hand in Dean’s shirt for a long moment. Dean didn’t know whether he wanted Cas to move away or to lean in more, but he knew that if Cas didn’t make a move in either direction soon, Dean would combust. He was about to say so, had opened his mouth to say so, but then Cas was taking a steadying breath and tugging the shirt up, eventually getting Dean to lift his arms so he could remove the shirt entirely.

Cas’s soft breath at seeing Dean’s bare torso bolstered Dean’s ego, but still, he felt a flush rise up his neck. He let Cas look his fill, mostly because he didn’t trust himself to touch Cas and stop. He dug his fingers into the sheets and didn’t let go.

After a few long seconds, Cas’s hands lifted. Dean braced himself, but Cas was only leaning in to touch Dean’s face. “I knew you were beautiful,” Cas whispered, “but now that you’re mine, you’re stunning.” Then his hands were skimming down Dean’s ribs, settling at Dean’s waist. Dean gritted his teeth. Cas kissed his forehead, and that was the only warning Dean had for what happened next: Cas hooked both hands on Dean’s shoulders and swung his body around to settle his weight on Dean’s thighs.

“Jesus,” Dean whispered, his head tilting back to hit the headboard because the alternative was to stare straight ahead, right at the glimpse of collarbones that Dean wanted so badly to drag his teeth over. “Warn a guy.”

Cas laid his forehead on Dean’s shoulder. “Sorry,” he said. “This is very new to me.”

Dean took a few calming breaths. Then, turning his head so he could sigh into Cas’s hair, he very hesitantly laid his hands on Cas’s waist. “And how do you like it so far?”

“It’s not enough,” Cas whispered, pulling a shiver from Dean when the implications sunk in.

“Do you want to keep touching me?” Dean asked, and hearing the words said out loud made them sound even dirtier than he intended.

Cas’s breath against Dean’s collarbone was scorching, and on the next breath, he said, “Yes. But I want you to touch me too.”

Dean couldn’t stop the oath that fell from his lips. “Yeah,” he said, unable to stop himself from sounding desperate. “How? How do you want me to touch you?”

“Don’t care,” Cas said breathlessly, his hands scratching lightly down Dean’s chest, making Dean grunt in surprise.

“You sure?” Dean gritted out, “There’s a lot of ways I can touch you, babe.”

Cas took one of Dean’s hands and guided it up under his shirt. “I’m asexual, not naive, Dean,” he said. His hips pushed forward. 

Whatever Dean had been about to say disintegrated on his lips when he realized that Cas was getting hard. “Off,” was all he could say then, as he pulled on Cas’s shirt. “ _Off_.”

The uncovering of Cas’s skin took Dean’s breath away. He was tan and lean and as beautiful as Dean had always known him to be. The idea that all of this skin was Dean’s to touch was overwhelming. 

But Cas had stopped touching, so Dean pulled his fingers back into his palms and put them back onto his lap, trying to ignore the one part of him that was aching for more. Cas’s eyes were wild and dark, but he moved slowly, carefully. He leaned forward and let his forehead fall onto Dean’s shoulder again. One arm came up over Dean’s other shoulder to pull Dean even closer by the hair. It hurt a little, but Dean felt Cas’s breath on his neck again, unsteady, and the pain paled in comparison to the knowledge that Cas was his, _his_ , and all Cas’s pain and pleasure and everything in between - that was Dean’s, too.

“You okay?” Dean breathed.

“Will you do me a favor?”

“Jesus. Anything.” 

Blindly, Cas reached for Dean’s left hand, still a fist by Dean’s hip. When he found it, he wordlessly guided it to the elastic of his borrowed pajama bottoms.

“Fuck,” Dean said helplessly. His other hand came up to grip Cas’s hip. “Are you sure, Cas?” he asked urgently. “Really sure?”

“I’ve had 16 years to think,” Cas said against Dean’s jaw. “I’m sure.”

Dean took a deep breath and did it before he lost his nerve - dipped his hand into Cas’s boxers and grasped the warm length of Cas’s dick, pulling it out and swallowing at the sight of it, thick and flushed and beautiful, swelling against the pull of Dean’s palm.

Cas was breathing slowly and heavily on Dean’s neck. When Dean started stroking, he heard Cas’s voice wrecked, destroyed: “love you, love you” and Dean turned his face into Cas’s hair and whispered it back, ignoring the way his voice cracked, concentrating instead on the twist of his wrist, the way Cas’s breath quickened when Dean swiped at the precome at the head of his dick, the way Cas’s hips started jerking forward.

“Never letting you go,” Dean said, when Cas got to the point where all he could do was grip Dean’s shoulders and shake and cry out with every pass of Dean’s hand. “Never.”

Cas groaned. He removed the hand that had been gripping Dean’s arm with all the force of a vice grip and wrapped it around Dean’s, directing Dean to squeeze a little harder, stroke a little faster.

“That turn you on, babe?” Dean breathed, delirious, laughing a little. “That I’m yours? That you’re gonna have this forever?”

Cas’s mouth was slack against Dean’s collarbone; another moan ripped loose.

Dean smiled, huffing a laugh into the air between their chests and licking his lips at the sight of Cas’s dick disappearing and reappearing between their joined hands. His own erection was impatient in his shorts, but the desire to get off was nothing compared to the desire to let Cas spill all over their hands for the first time. He pressed a kiss to Cas’s sweaty temple and studied the bow of Cas’s back, the muscles that tightened every time he shoved his hips forward. He couldn’t see Cas’s face, but he could imagine it just fine: a mess of pleasure and frustration in every clench of his jaw, every lick of his lips, every furrow of his brow. The sounds Cas was making against Dean’s neck were obscene - quiet grunts and swallows between breaths that shook that sent shivers down Dean’s spine.

When Cas came, it was with a long groan that he tried to muffle in Dean’s neck. Dean let him control the pace as he rode through orgasm, enjoying the way Cas’s hand clenched around his, how Cas demanded his pleasure and trusted Dean to give it. 

When Cas stopped shaking and finally let their hands fall away from his dick, Dean turned his face into Cas’s temple. “You good?” he whispered.

Cas’s breath was still shallow. He nodded jerkily, his face still burrowed in Dean’s neck. 

Dean cleaned them up with his T-shirt, then ran his hands down Cas’s back. “We - uh. We gonna do that again sometime?”

Cas was silent for so long that Dean started thinking of all the future lonely jerk-off sessions he’d be indulging in. He comforted himself with the thought that at least he’d been able to make Cas come once in this short life, and that the memory was forever his to jerk off to. 

But then Cas was lifting his head and there was a hand grasping Dean’s dick through his boxers and Dean thought _oh._

Cas’s lashes were studded with moisture - sweat or tears, Dean couldn’t tell - but his eyes were dark. Dark and wild. He leaned in and spoke the next words against Dean’s mouth: “If by ‘sometime,’ you mean _right now_ , then yes, Dean, we’re going to do that again _sometime_.” 

Dean was about to make a dry remark about Cas’s sass, but then Cas’s hand was in Dean’s boxers and suddenly Cas’s sass didn’t matter.

 

After, they slept. Then Cas woke Dean up in the middle of the night and told him, in very direct terms, that Dean needed to call in tomorrow because Cas had some very specific plans. Most of the plans involved staying in bed and decidedly _not_ sleeping.

“You’re perfect,” Dean whispered into Cas’s shoulder.

Cas was silent, and Dean guessed why.

“Not because you’re willing to sleep with me,” he added. He kissed Cas’s jaw. “You’re perfect even without your hand in my pants.”

Cas swallowed; Dean heard it. He waited.

“Earlier - did you mean it?”

Dean lifted his head to see a flush on Cas’s face. “Mean what?”

Cas looked away. “‘Forever.’”

Dean sat up. “Cas,” he said. “Dude.”

“What?” Cas said, scowling a little. “I didn’t know you had feelings for me until yesterday. How am I supposed to know what’s - ”

“What’s real?” Dean leaned down. He waited for Cas to look at him, then he kissed him. He would never get tired of it. “Babe,” he said, indulgent in the afterglow. “You know me. You know I’d never make a decision like this without knowing it’s what I wanted.”

“So you _meant_ to ask me to marry you,” Cas said, squinting a little.

“I didn’t technically ask you,” Dean said, grinning. “I said I’d propose, but I didn’t actually propose.”

Cas scowled. “I wouldn’t say yes anyway.”

Dean laughed. He planted himself on Cas’s thighs and leaned over the love of his life. “And if I called your bluff?”

Cas’s scowl vanished, replaced very quickly by a wide-eyed look. The flush returned, but now it spread down to his chest. “I’d - I’d say no.”

Dean shook his head. Laughed. “No, you wouldn’t.”

“I would.”

Dean leaned down further and nudged their noses together. His hands spanned across Cas’s ribs. “No,” he said firmly. “I don’t deserve it, but you’d say yes.”

Cas shook his head. “Stop talking like that. You deserve everything.”

“So you’re saying yes.”

Cas sighed. It was a beautiful sound. “You’re manipulating me.”

“That’s a yes.”

“You haven’t even asked me, Dean.”

Dean sat up. He touched Cas’s face, looked down to where the flush was almost down to Cas’s navel. He was in love with Cas. And he was going to marry Cas, if Cas said yes. “Cas, will you marry me?”

Cas’s lips were pressed tightly together, his nose a little pink. He sniffed. “Are you sure?”

Dean rolled his eyes. “I’ve had 16 years to think.”

Cas sent him a dry look, though it was somewhat undercut by the pink of his nose. “No, you haven’t. You haven’t even had six weeks.”

Dean bit down on a scowl. It was true, but it didn’t make the sentiment any less real. “More than enough time to know I don’t want to spend the rest of my life without you.”

Cas swallowed. Dean watched his eyes dance between his own. Finally Cas said, “Yes. You asshole, you know it’s a yes.”

 

**Author's Note:**

> DCBB Masterpost (will be updated with a link when the post goes up)  
> Art masterpost: [link](https://bs-acorns.tumblr.com/post/179130367893/art-masterpost-for-if-i-loved-you-less) (may not be public at the time of your reading)
> 
> Thank you so much for reading! It was a journey, wasn't it? I have to be honest - I'm not entirely happy with everything, but I did definitely enjoy writing it - even if it IS my longest fic to date.
> 
> Thank you again to Busy, and to my cousin Jay for beta-reading. 
> 
> ALSO follow me on [tumblr](https://surlybobbies.tumblr.com) and [twitter](https://www.twitter.com/surlybobbies)!
> 
> Let me know what you thought!


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